Ross Alcorn

Our Mission Empower business owners, entrepreneurs, real estate investors, and busy professionals to turn everyday business and personal spending into premium points-and-miles-powered travel, dramatically reducing travel costs by 90% or more. What We Do We don't book your trips—we equip you with a proven, repeatable framework to earn, plan, and redeem travel rewards like a seasoned pro. Our personalized systems eliminate the overwhelm, saving you thousands of dollars and countless planning hours. Why Choose Itinerary Boss? Founded by a former medical-device and healthcare software sales executive, entrepreneur, and real estate investor who’s planned personal and business trips across 20+ countries, we've turned real-world experience into simple, actionable strategies. How We Help You Win ✅ Personalized Card Blueprint Pinpoint the exact business and personal credit cards tailored to your unique spend patterns and travel goals, maximizing every swipe. ✅ Earn-More Engine Unlock advanced strategies to earn 2–10x points on the cards you already use. Layer transfer bonuses and strategic spending for massive rewards. ✅ Redeem-Like-a-Pro Roadmap Turn points and miles into premium flights and five-star hotel stays at a fraction of retail cost with step-by-step, proven frameworks. Multi-Channel Learning: 🎙 Podcast – Multiple weekly episodes 🗺 Blog & Destination Guides – Curated sample itineraries and points-and-miles strategies. ✉️ Weekly Newsletter – Concise tips, timely award alerts, and actionable insights delivered directly to your inbox. 💬 Daily LinkedIn Tips & Case Studies Free Resources 🎁 Points & Miles Cheat Sheet (PDF) 🎁 Stress-Free Travel Starter Kit 🎁 Destination Playbooks & Sample Itineraries Premium Services Free 1-on-1 Credit Card & Spend Strategy Consultations – Personalized sessions designed to maximize returns on your business and personal spending. Ready to Transform Your Spend into Luxury Travel? Visit itineraryboss.com