If You’re Spending $10,000+ Per Month
You Shouldn’t Be Paying Cash for Travel.
Install a clean rewards architecture so your business funds premium flights, hotels, and family trips without adding complexity to your life.
👉 Get The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There
Spending $30K+ monthly? → Apply for a Spend Snapshot
For business owners who value leverage over convenience.
The Silent Leak in Most High-Spend Businesses
At $10K+ per month, small inefficiencies compound.
At $30K+ per month, they quietly turn into five-figure losses.
It usually looks like this:
Writing $12k–$20k checks for flights
Booking hotels or Airbnbs at retail cash prices
Redeeming points for statement credits, gift cards, or Amazon
Letting assistants default to bank portals for poor value
Paying vendors by ACH or check without questioning it
Flying coach because there is no strategy
You’re earning.
But you’re not engineering.
Convenience keeps beating leverage.
If Nothing Changes…
You’ll keep paying retail
Points will pile up with no real plan — and slowly devalue
Travel will feel random and reactive
Your spouse will enjoy the trip — but you’ll feel the bill
You’ll keep telling yourself you’ll “optimize it later”
Most never do.
At your level of spend, that’s unnecessary.
Install Foundation Once.
Let It Run.
We don’t teach overwhelming travel hacks.
We install systems.
Inside the Operator Framework, we:
Diagnose your current spend + card setup
Design a clean business + personal architecture
Create simple routing rules for you and your team
Align points with specific premium trips
Install guardrails so bookings happen correctly
This becomes a system.
Not a side hobby.
Not another thing you have to keep up with and manage daily.
Why Businesses Work With Itinerary Boss
Real People. Real Results.
Kevin Riggi
Real Estate Investor & Business Owner
Before:
Multiple cards.
No system.
Vendor spend felt random.
After installing structure:
Aligned cards to software, advertising, and vendor expenses.
Points finally funded meaningful travel instead of sitting idle.
“Trips that felt like ‘maybe someday’ became realistic for my family.
Our business spend is finally working for us.”
Mike Misleh
Vice President
Before:
Running business spend through one card.
No clarity. No redemption strategy.
After installing architecture:
Aligned personal + business spend.
Maximized partner transfers.
Unlocked premium travel redemptions with confidence.
“The biggest difference is confidence. Everything
is simple, organized, and repeatable.”
Lauren Ross
Senior Manager
Before:
Booking through portals. Sitting on points without clarity.
Within 30 days:
Leveraged existing balances properly.
Transferred strategically.
Booked 11 nights in Europe within 30 days saving over $5,000 in cash value.
“Working with Ross was a game changer in learning how far our points can really go.”
Lauren Perussault
Senior Account Executive
Before:
Overwhelmed. DIY research for years.
Never confident enough to pull the trigger.
Within 90 days:
Opened two aligned cards.
Hit welcome bonuses.
Saved ~$4,000 on a St. Lucia honeymoon.
“Strategizing saved us almost $4,000 on a trip of a lifetime.”
Two Ways to Start
Path 1 — Start Here
Get the 5-Step Roadmap
Understand how structured leverage works.
See where you may be leaking value.
Path 2 — I’m an Operator
Spending $30K+ per month?
Apply for a Spend Snapshot.
We’ll review your current set up and show you exactly where money is being lost.
If you’re a fit, we install the full Operator system inside The 5-Star Travel Points Operator Program.
We don’t accept everyone.
Same Spend
Different Architecture
One person:
Pays retail
Books “fine” hotels
Flies coach
Cashes out points
Makes expensive cash vacations
Keeps putting those trips off because “travel’s expensive”
The other person:
Flies business class.
Stays oceanfront in suites
Funds bucket-list family trips on points
Turns daily expenses into first class flights & 5 star hotel stays
The difference isn’t your spending.
It’s your structure and strategy.
If you’re serious about turning spend into leverage…
👉 Get the The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There