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.'s order: guest, then market, then property.
"Falling in love with a house first is the most expensive mistake in this business."
Guest example: about 2 million U.S. couples married in 2025, 117 guests on average (The Knot).
Free guide: go.cashflowdiary.com/m29-wed…
When the sale closes before the new house does, a family needs a place for the gap.
Buyers and sellers between homes are 1 of 66 guest types. They come through realtors, lenders and movers.
Fits a host who knows local agents.
Free guide: go.cashflowdiary.com/m29-bet…
Thanksgiving is four weeks from today. AAA projected a record 81.8 million travelers for it last year.
Many families have more relatives coming than beds.
Holiday overflow is 1 of 66 guest types. Fits a host in a neighborhood.
Free guide: go.cashflowdiary.com/m29-hol…
Nights booked in 28+ night stays: 20 million in 2019, 46 million in 2025 (AirDNA + Furnished Finder).
Remote workers picking a city for a season are 1 of 66 guest types.
Fits a host with a real desk and fast Wi-Fi.
Free guide: go.cashflowdiary.com/m29-rem…
Extra income without a second job starts with who already needs a bed near you.
The Pentagon moves about 300,000 military and civilian households a year (Military.com).
Near a base, families on new orders are 1 of 66 guest types.
Free guide: go.cashflowdiary.com/m29-pcs…
J. Massey's course: "You can't make money. If you and I make money, it's illegal. It's called counterfeiting."
"You and I have to earn it, and the only way to earn it is to create something of value and learn to sell it."
Free diagnostic call:
go.cashflowdiary.com/m28-ear…
54% of Americans say they are saving less for emergencies because of inflation (Bankrate, Jan 2026).
If your emergency fund stopped growing this year, more than half the country is with you.
Free newsletter on building a second income:
go.cashflowdiary.com/m28-inf…
The biggest line in a rental arbitrage launch budget is the furniture.
For a two-bedroom we plan $4,600 to $7,400. Beds, sofa, kitchen, linens. More than the deposit and first month's rent combined.
Free diagnostic call:
go.cashflowdiary.com/m28-fur…
#RentalArbitrage
Only 30% of Americans say they would pay a $1,000 emergency from savings. 33% would go into debt to cover it (Bankrate, Jan 2026).
One car repair can turn into months of payments.
Free newsletter on building a second income:
go.cashflowdiary.com/m28-100…
J. Massey's course homework: watch a shopping channel for 30 minutes. Notice when "I would never buy that" turns into "Maybe I could find a use for that."
His point: "You can only get them to want to do it."
Free call:
go.cashflowdiary.com/m27-sho…
On Airbnb and another site? Airbnb updates imported calendars every 3 hours (Airbnb Help). Until then, nights booked elsewhere can still look open on Airbnb.
Tap Refresh on the connected calendar when a booking comes in.
Free host newsletter:
go.cashflowdiary.com/m27-ica…
The average one-way commute in the U.S. is 27.2 minutes, up from 26.8 the year before (Census, 2024 ACS).
That's about 54 minutes a day getting to and from work, and for most people it's unpaid.
Free newsletter on building a second income:
go.cashflowdiary.com/m27-com…
Airbnb can block 1 or 2 nights before and after every reservation for you. That's preparation time. Advance notice can be same day, or at least 1, 2, 3 or 7 days (Airbnb).
Set both from your cleaner's real schedule.
Free call:
go.cashflowdiary.com/m27-pre…
The average U.S. household is projected to spend $1,030 to heat their home this winter, up $82 or 8.7% from last year (NEADA, 2026-27 outlook).
That bill lands on top of the holidays.
Free newsletter on building a second income:
go.cashflowdiary.com/m27-hea…
J. Massey's three words that stop people from learning: "I know that."
In his course: "Soon as you say words like, 'I know that,' guess what you're not doing. You're not learning."
When you hear yourself say it, ask one more question. Free call:
go.cashflowdiary.com/m26-ikn…
Airbnb bans open-invite parties and disruptive gatherings of any size. Hosts can't advertise a listing as party friendly.
It watches for excess noise, trash and parking trouble, and may block bookings it sees as higher risk.
Free newsletter:
go.cashflowdiary.com/m26-par…
29% of buy now, pay later users say they've used it for groceries, up from 14% two years ago. 47% paid late in the past year (LendingTree, 2026).
Free newsletter on adding a second source of income:
go.cashflowdiary.com/m26-bnp…
Airbnb fees when a host cancels a confirmed booking:
30+ days before check-in: 10%
48 hours to 30 days: 25%
48 hours or less: 50% of unstayed nights
$50 minimum, usually taken from your next payout.
Free diagnostic call:
go.cashflowdiary.com/m26-hos…
#AirbnbHost
People out of work in the U.S. had been looking 24.8 weeks on average in September. The median was 11.5 weeks (BLS).
That's the stretch savings has to cover if a job goes. Free newsletter on income that doesn't hang on one employer:
go.cashflowdiary.com/m26-job…
From J. Massey's course: "Many people say the most difficult thing is getting started. I think the most difficult thing is actually staying started."
His question for a Sunday night: "Come Monday, are you still started?"
Free diagnostic call:
go.cashflowdiary.com/m25-sta…
