STR Diagnostic + Custom 90-Day Plan

Turn the rental that runs you into a business you run, from anywhere

Find out exactly where your rental leaks money and time, and get a 90-day plan that fixes it in order, built on your numbers. It starts with a free 25-minute call.

Book your complimentary one-on-one diagnostic call

Free, 25 minutes. The full plan is $997, one time, and I'll only offer it if it fits. No is a fine answer.

Shirley Wilson

“I'm actually retired. This month we hit $20,000 in revenue.”Shirley Wilson, Oceanside, CA · watch her story · monthly revenue, not profit

Where a $1,000 stay can go
Booking site fee~$155
Manager~$200
Left for you, before costs~$645
Example only: a 20% manager and a ~15.5% host fee. Your numbers will differ.
Sound familiar?

If two of these are true, keep reading

Platform and management fees come off the top before you see a dollar.
Cleaners and caretakers miss things when you're not there, and every fix costs extra.
You have past guests' contact details, but no way to bring them back.
You're not sure what the place really makes after every cost.
The calendar goes quiet when the season ends.
You're the one holding it all together, from your phone.
What the diagnostic finds · Part 1

Your income comes down to four things

We measure each one on your numbers and find which leaks most, so you fix that first instead of guessing.

1

More people find you

Beyond what one booking site decides to show.

2

More of them book

Fewer questions that go unanswered or go cold.

3

They come back

Past guests return, and bring friends.

4

You keep more

Of every stay, after fees, cleaning and the little leaks.

+46%

They multiply. Get 10% better at all four and you earn about 46% more. That's plain arithmetic, shown as an example only. It's also why fixing the right one first matters.

What the diagnostic finds · Part 2

Every job, and who really owns it

We list the jobs that keep a rental running and who does each today. The ones marked below are where most owners lose money and sleep. Each gets an owner: a person with a clear checklist, or something set up to run on its own and follow up until it's done.

JobWho does it todayWhat slips
Checking each turnover is doneThe cleaner, when reachableNobody confirms
Answering guest questions at 11pmYouSlow replies
Offering extras guests would pay forNobodyNever offered
Inviting past guests backNobodyGuests forget you
Totaling the month's numbersNobodyFound out at tax time
What the plan gives you

And what it means for you

More people find you

You getWhich past guests to reach first, and a simple content plan for new kinds of travelers.
It doesLess dependence on one booking site or one manager.
Which meansYou choose who comes, instead of hoping the algorithm sends someone.

More of them book

You getWhere people who ask go quiet today, and a book-direct offer for past and referred guests.
It doesMore questions turn into paid nights.
Which meansThe calendar doesn't go quiet when the season ends.

They come back

You getWhen and how to invite past guests back, and how to ask for referrals.
It doesMore stays a year from people who already trust you.
Which meansSteadier income, with less spent finding each guest.

You keep more

You getA clear job list for each person, extras guests want, and a monthly numbers habit.
It doesFees and small leaks shrink.
Which meansNumbers you trust, from a business that earns what it should.
Why $997 can pay for itself
1 guest
Every booking-site stay gives away a share to fees. Bring one past guest back direct and most of that share stays with you. That's one change. Your plan will have several.
The small stuff, handled without you

What can run on its own

Common examples the job list points to. Anything involving money stays with you.

Guest questions, answered

Routine questions answered in minutes, day or night, with your extras offered.

Turnovers, confirmed

The checklist goes out after every checkout, and it keeps following up until each item is done.

Your numbers, totaled

Bookings and costs added up every month, so you know what you really make.
From a Cashflow Diary client

What it looks like when the pieces fit

“I'm actually retired. This month we hit $20,000 in revenue, and we've only been in business for a few short months.”
Shirley Wilson, Oceanside, CaliforniaMonthly revenue, not profit. Results depend on your property, market and follow-through.
How your plan is built

From your why down to week 1

  1. 1Your why. Where you want this business to be, and why.
  2. 2One goal. A 12-month profit goal, with one number for each of the four.
  3. 3The approach. What the booking sites are for, and what you own directly.
  4. 490 days of moves. The few projects that matter most, in order.
  5. 5Checklists and job lists. So everyone knows what "done" means.
  6. 6A weekly scorecard. One screen that shows if the plan is working.
  7. 7Week 1. Who does what first, and what runs on its own.
How it works

Four steps

Step 1Complimentary one-on-one diagnostic call25 minutes with me. We look at where the business stands and whether the plan fits. No is a fine answer.
Step 2Intake75 short questions in 10 sections, about 3 hours.
Step 3Your planAbout 96 hours after you submit the intake.
Step 4Plan review callWe walk through every step together.

Pick your time

Calendar not loading? Open the booking page.

Questions

Is this just generic AI? Couldn't I ask ChatGPT?

You could, and you'd get the same answer as everyone else who types the same question. This starts with about 75 questions about your property, your numbers and your goals. Then I research your market myself. The plan is built from your answers, not a template, and we go through every step of it together on a call. AI helps us work faster. The decisions in your plan come from me and from your numbers.

Will I need new software?

Maybe. Many owners start with none, just a booking site and a phone. The plan names only the software that closes a real gap, what it costs, and why, before you buy anything. That can include our own Book Them Twice. If you already use a system like Hospitable, the plan builds on it.

I already use Hospitable, Guesty or similar. Is this the same thing?

No. Those run reservations, calendars and messages. The diagnostic looks across your whole business, including those tools and the people you pay, to find where money and time leak and what to fix first. Here's how Book Them Twice fits next to those tools.

Do I have to live near the property?

No. The plan is built so you can run it remotely. I run my own properties from West Palm Beach.

I have a property manager. Is this still for me?

Yes. Most owners keep their manager. The plan makes clear what each person does and what you're paying for.

What does it cost?

$997, one time, for the diagnostic and your custom 90-day plan.

What happens after the plan?

You can run it yourself. If you want support, there's a group option where small operators meet with me and the team every week.

Find your biggest gap in 25 minutes

Bring your rough numbers. You leave with your first move, whether or not we work together.

Book your complimentary one-on-one diagnostic call
J. Massey · Cashflow Diary · Strategies that turn opportunities into income. Results depend on your property, market and follow-through. No earnings are guaranteed.