Business Credit Cards, Points, & Miles with Ross Alcorn, Itinerary Boss #213
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
Common Mistakes to Avoid:
- Not asking vendors if they accept credit cards
- Using wrong card for spending category (leaving 2-3x points on table)
- Redeeming points poorly (gift cards, statement credits)
- Not tracking card benefits and credits
- Waiting too long to book award travel
- Not being flexible with dates/airports
Tools & Resources Mentioned:
- Points.Yeah.com - Award availability search, flight ideas map
- Melio - Pay vendors via card when they only accept ACH
- Plastiq - Pay rent/large bills with credit card (2.9% fee)
- Free Points & Miles Cheat Sheet at ItineraryBoss.com
- Transfer partner guide and credit card multiplier sheets
Key Quotes
"There's millions of dollars that aren't being put on cards because of just not asking the right questions."
"If you're earning 2x points and utilizing those points to transfer, even with a 3% fee, the numbers pencil when you're redeeming at 2-6 cents per point."
"175,000 Amex points could be used to get you business class, first class seats - we used 176K Chase points for $12,700 worth of business class seats to South Africa."
"Don't redeem for Amazon gift cards, statement credits, or through the portal - you're getting 0.6-0.7 cents per point. That's terrible."
"Why give a $10K cash bonus when you could give someone 500K miles and book them a trip to Greece or Bali they'd never do on their own?"
Who This Episode Is For
- Military small business owners and real estate investors
- Service members with TDY/TAD travel
- Anyone spending on business ads, inventory, or vendor payments
- Military spouses running 1099 contractor businesses
- People planning big trips (honeymoons, bucket list travel)
- Those currently leaving business value on the table
- Anyone wanting to turn business expenses into free travel
Action Items
- Sign up for all major hotel loyalty programs today (free)
- Add loyalty numbers to upcoming TDY stays
- Check if vendors accept credit cards (or use Melio)
- Review current card stack - are you earning maximum points per category?
- Download free cheat sheet at ItineraryBoss.com
- If planning big trip: Start building points 1-2 years ahead
- Check military annual fee waivers (MLA/SCRA)
- Combine household points before booking award travel
Contact
Guest: Ross Alcorn
- Website: ItineraryBoss.com
- Free Points & Miles Cheat Sheet (includes transfer partners + credit card multipliers)
- Social: @ItineraryBoss (all platforms)
Host: Spencer Reese
- Website: MilitaryMoneyManual.com
- Instagram: @MilitaryMoneyManual
Recorded on Veterans Day. This episode reveals how military service members can leverage business expenses, TDY travel, and strategic credit card use to fund dream vacations. Whether you're spending $10K or $1M annually on your business, there are points being left on the table.
Spencer and Jamie offer one-on-one Military Money Mentor sessions. Get your personal military money and personal finance questions answered in a confidential coaching call. militarymoneymanual.com/mentor
Over 20,000 military servicemembers and military spouses have graduated from the 100% free course available at militarymoneymanual.com/umc3
In the Ultimate Military Credit Cards Course, you can learn how to apply for the most premium credit cards and get special military protections, such as waived annual fees, on elite cards like The Platinum Card® from American Express and the Chase Sapphire Reserve® Card.
Learn how active duty military, military spouses, and Guard and Reserves on 30+ day active orders can get your annual fees waived on premium credit cards in the Ultimate Military Credit Cards Course at militarymoneymanual.com/umc3
If you want to maximize your military paycheck, check out Spencer's 5 star rated book The Military Money Manual: A Practical Guide to Financial Freedom on Amazon or at shop.militarymoneymanual.com.
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