Ross Alcorn

Points, Cards and Travel

Society EN ↓ 159 episodes

Points, Cards and Travel is your weekly guide for business owners, investors, and high income professionals who want to earn more on everyday spend, learn powerful strategies no one taught you and turn points into luxury travel every year. Hosted by Ross Alcorn, each episode breaks down credit card strategy, smart systems, and real world examples so you can maximize rewards, improve cash flow, and unlock premium flights and hotels. Hear from points experts and lifestyle entrepreneurs who have done it and learn how to build strategic plans to save big and elevate every trip.

Author

Ross Alcorn

Category

Society

Podcast website

itineraryboss.com

Latest episode

Jul 8, 2026

Where to listen?

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Episodes

How to Get Free Hotel Upgrades Every Time: Ben's Big Deals on Hyatt, Hilton, Marriott, and the Email Trick Hotels Don't Want You to Know with Ben Komenkul 08.07.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the...

How to Plan a Stress-Free Trip: Flight Alerts, Travel Apps, and the Documents You Can't Afford to Forget 01.07.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the...

How Business Owners Turn Everyday Expenses Into Free Family Vacations 24.06.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the...

The $580,000 Mistake That's Quietly Draining Business Owners' Travel Budgets 17.06.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the...

Why Your Business Should Accept Every Form of Payment and How to Use That Spend to Fund Your Next Trip With David C. Barnett 10.06.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the...

How Homeowners and Landlords Can Earn Massive Points on Real Estate, Renovations, Contractors, and Mortgage Payments With Ross Alcorn 03.06.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the...

How to Maximize Points on Everyday Spending: Best Credit Cards for Groceries, Dining, and Travel Rewards Explained 27.05.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the...

How We Used Points To Save Over $19,000 On Our Honeymoon To Thailand and Bali 20.05.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the author'...

How to Unlock Unlimited 2-for-1 Flights with Southwest Companion Pass Using Points, Credit Cards, and Simple Planning 13.05.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the...

9 Credit Card Mistakes Beginners Make That Kill Points Value and How to Turn Them Into Free Travel 06.05.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the...

How to Turn Business Spending into Free Travel: Credit Card Points, Miles, and Smart Strategies for Military Members and Entrepreneurs 29.04.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the...

How Danny Safran Turned Credit Card Points Into Family Trips, Luxury Hotels, and Europe Getaways Without Working in Travel 22.04.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the...

The Power of Welcome Offers: How To Earn More Points, Avoid Bad Redemptions, and Turn Everyday Spend Into Luxury Travel 15.04.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the...

The Hardest Part of Points Travel: Finding Award Availability with Kyle Potter from Thrifty Traveler 08.04.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the...

Zero Percent Business Funding: How Entrepreneurs Use Credit Strategy, Higher Limits, and Smart Banking to Grow Without High Interest Debt 01.04.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the...

The Hidden Strategy Behind Business Credit Cards: Use Spending, Billing Cycles, and Points to Unlock Travel and Business Flexibility 25.03.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the...

How Business Owners Use 0% Interest Credit Cards to Invest in Growth, Reduce Financial Stress, and Earn Travel Points Along the Way 18.03.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the...

From One Card to Luxury Travel: How Smart Points Strategy Saved $4,000 on a Honeymoon 11.03.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the author'...

Your First Female Solo Trip Blueprint: Safety Tips, Travel Trends, Travel Insurance, and Points Strategy with Henah Velez 04.03.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the author'...

How she saved $4,000 on a United Kingdom and Ireland Trip Using Points: Transfer Partners, Sweet Spots, and Smarter Booking Tips with Lauren Ross 25.02.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the...

BILT 2.0 Rewards Explained: How to use Rent and Mortgage Payments to fund free travel with Henah Velez 18.02.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the author'...

How Home Renovations With 0% APR Cards Funded a $6,000 Hawaii Trip on Points with Chris Reichenbach 11.02.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as ⁠ YourBestCreditCards.com⁠ . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the author'...

How to Earn Maximum Credit Card Points, Hotel Room Block Rewards, and Plan a Stress-Free Destination Wedding with Kerry Krull (The Wedding App) 04.02.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the au...

Why 40–50% of Flights Drop After Booking and How SkyKey Automatically Gets You the Difference Back with Jacob Goldberg, Co-Founder SkyKey 28.01.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the au...

Positioning Flights Explained: How to Unlock Business Class Awards From Any Airport with Hunter Threadgill from Professor of Points & Frequent Traveler University 21.01.2026

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com . This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the au...

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