Client Testimonials

Explore real stories from business owners, senior managers, and high-income professionals who have transformed everyday spend into premium travel through structured card and payment strategies, with clear examples, measurable results, and a repeatable system that turns inefficiency into opportunity.

Kevin Riggi

What changed was having a clear system. Ross helped me align the right cards with the right expenses, showed me how to pay vendors in ways that earned points more efficiently, and most importantly, how to convert those points into real trips instead of just numbers sitting in an account.

Stella Hennessy

After learning about Itinerary Boss, I used resources like the cheat sheet and newsletter to plan our trip. With Ross’s guidance, my husband and I booked our international round-trip honeymoon flights in the highest fare class completely for free.

Mike Misleh

Ross helped me put a clear strategy in place that fit both my personal life and our real estate business. Not just for everyday spending, but also for when we needed extra flexibility or float while furnishing properties and getting things up and running.

Lauren Ross

“On my Europe trip, I saved nearly $4,000 on flights and hotels just by using the right strategy.”

Stella Hennessy

“Before this, I just thought credit cards were for points. I had no idea how much more value I could actually get out of them.”

Lauren Perussault

“I spent five years overthinking credit cards, and within months of working with Ross, we saved over $4,000 on our honeymoon.”

$5M spend a Year… And It Was All Going to Waste

Brendan from Dapper Development was running millions through credit cards with no real strategy, relying on simple cash back and leaving significant travel value on the table. Within just four months of installing the right structure, he generated over 2.1 million AMEX points, booked a trip to Aruba, and is now planning a Europe trip, all by aligning the right cards, optimizing payment flow, and turning everyday business spend into a predictable system for premium travel.

  • “We were spending $5M+ a year and barely getting anything back. In just a few months, we’ve already generated over 2 million points, taken a trip to Aruba, and now have a clear plan to turn our business spend into real travel experiences.”
    Brendan Gelson
    Dapper Development llc

  • “I Thought I Was Maximizing Points. Until I Realized How Much I Was Leaving on the Table”

    “Before Itinerary Boss, I thought I had an efficient strategy. I was acquiring cards and hunting point bonuses, but I was only using the portals for gift cards, cash back, or the occasional flight or hotel portal. After connecting with Ross, I realized the amount of potential I left out there not using transfer partners. I joined his newsletter and it’s been a game changer ever since!“
    Anthony Fraraccio
    Underwriting Assistant