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Spencer Reese welcomes Ross Alcorn from Itinerary Boss https://itineraryboss.com/ to discuss credit card points and miles strategies, with special focus on small business owners. Ross shares how he saved $19,000 on his honeymoon, reveals tactical business spending strategies, and explains how military service members can leverage TDY travel and small business expenses to fund dream vacations. Guest: Ross Alcorn - Charlotte, NC-based travel strategist, former sales rep road warrior (6-7 years), real estate investor, and founder of Itinerary Boss. Key Topics Covered Getting Started - The Low-Hanging Fruit: • Sign up for FREE hotel loyalty programs (Hilton, Marriott, IHG, Hyatt) • Add loyalty numbers to TDY/TAD stays retroactively if needed • Military discount: Epic Pass for active duty/spouses ~$200 (normally $1,200) • Start with no annual fee cards to build credit and learn the basics • Never carry a balance - if you're paying interest, you're doing it wrong Business Spending Strategies: • Most common mistake: Using Amex Platinum for everything (only 1x points on most purchases) • Capital One Venture X Business: Uncapped 2x points, no preset credit limit • Cards earning 3-4x on ad spend (Facebook, Google ads) • Use Melio (M-E-L-I-O) to pay vendors who don't accept cards via ACH (2.9% fee) • Negotiate early payment discounts (net 15 vs net 30) to offset processing fees • Millions in business expenses going uncharged to credit cards The 2.9% Fee Debate: • Worth it if redeeming points at 1.5+ cents per point value • Effective 25-40% cash back when factoring welcome bonuses + transfer value • Business expenses are tax deductible • Ross personally pays fees on all expenses knowing he'll redeem at 2-6 cents/point Real-World Example - $19,000 Honeymoon Savings: • Cards used: Chase Sapphire Reserve, Capital One Venture, Chase Sapphire Preferred, Chase Ink Business Unlimited • Flights: Qatar Q-Suites business class using 200K points (Chase + Capital One) • Stayed 11 nights using Hyatt points at Alila properties in Bali • Built point stash over 1-1.5 years through group travel booking + daily spend + business welcome bonuses • Strategy: Booked award availability 355 days out when British Airways/Qatar released schedules • Flexibility: Mixed business and premium economy on return flight Transfer Partners & Redemption: • NEVER redeem for Amazon gift cards, statement credits, or low-value portal bookings (0.6-0.7 cents/point) • Transfer to airline partners for 2-6+ cents per point value • Don't use Amex points for hotels (poor value) • Example: 175K Amex points = potential $12,700 business class seats to South Africa • Tools: Points.Yeah.com for flight availability and award searching Military-Specific Advantages: • Overseas duty stations = less competition for award space (Frankfurt, Tokyo, Seoul) • Different inventory than US-based flyers • TDY/TAD stays earn hotel points and elite status • Annual fee waivers on personal cards (not business cards) via MLA/SCRA • Chase Sapphire Reserve: $0 annual fee for military/spouses Strategic Tips: • Always volunteer to pay group bills/dinners (earn points, get reimbursed) • Premium economy fine for daytime flights under 8-9 hours • Business class essential for overnight/long-haul flights (9+ hours) • Plan 1-2 years ahead for big trips - comfortable pace to build points • Opening velocity: Ross did one card every 91 days at peak (very aggressive) • Combine household points (Chase, Amex, Capital One allow this) • Book tickets in anyone's name, not just your own Credit Card Stacking Strategy: • Don't use one premium card for everything • Match card to spending category for maximum points • Chase "cash back" cards earn Ultimate Rewards points if you have Sapphire Reserve/Preferred • Transfer between household members before booking • Welcome bonuses are the real value - daily spend is bonus Business Culture Hack: • Instead of $5-10K cash bonus, give employees 500K miles + book their dream trip • Tax deductible, builds culture, retains talent • More memorable than cash bonus IHG Five Free Nights Strategy: • Five free nights at properties up to 60K points/night • Ross staying 4 nights in Grand Cayman at $800/night hotel = $3,200 saved • Fourth night free on award bookings • Anniversary free night each year • Used for wedding block, earning 26x points on wedding expenses ...