About Ross
What I Do
I’m Ross, founder of Itinerary Boss.
I help busy professionals and business owners turn the money they’re already spending into real travel — without guessing, hoarding points, or wasting value. I’m not a travel agent.
I don’t book trips for you. I teach a simple, repeatable system so you can earn and redeem confidently on your own.
Most people don’t have a spending problem. They have a planning problem. That’s what I fix.
Why This Exists
I’ve been on both sides — traveling constantly in healthcare and software sales, building businesses, investing in real estate, and trying to make the most of limited time.
What I kept seeing was the same thing everywhere:
- People earning points without a strategy
- Redeeming them the wrong way
- Leaving thousands in value on the table every year
No company I worked at ever taught this even though it impacts some of our biggest monthly expenses.
That gap is why I built Itinerary Boss.
How I Help
I help you:
- Earn more from everyday spend you already have
- Choose the right cards without overcomplicating it
- Avoid common redemption mistakes that quietly waste value
- Turn points into travel you’d otherwise pay cash for
The goal isn’t more cards.
The goal is clarity, flexibility, and fewer decisions.
Simple beats perfect.
Proof It Works
I’ve personally saved over $50,000 in the last year in travel using the same frameworks I teach. I’ve also helped many professionals and business owners do the same — without turning this into a second job. Check out our testimonials page to see what people are saying:
“Ross clarified exactly which cards matched our goals and how to redeem properly. We’re now saving over $3,000 on hotel stays we would’ve paid cash for.” — Lauren & Brady
How to Get Started
You have two easy options
