Points, Cards and Travel

Ross Alcorn

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.

  1. 2d ago

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

    (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's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired. In episode 154 of Points, Cards and Travel, most business owners avoid credit cards for vendor payments because of the 3% processing fee, but that mindset could be costing them millions of points. In this episode, Ross breaks down how tools like Plastiq and Melio let you pay contractors, vendors, and service providers who only accept cash or check using a credit card, unlocking massive points-earning potential.  Ross walks through real numbers: a $580,000 annual spend turning into $46,000+ of travel value, and how scaling to 3-5x multipliers can push that even higher. Whether you're a real estate investor, house flipper, or business owner working with old-school vendors, this episode shows you how a simple two-card stack and the right software can transform routine expenses into life-changing travel rewards.  Credit Card Resources: ⁠5 Step Roadmap⁠ to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Best Credit Cards for Travel Melio: Pay vendors who don't take card with credit card to earn more points Itinerary Boss Socials: ⁠LinkedIn⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.   Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

    16 min
  2. Jun 10

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

    (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's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired. In episode 153 of Points, Cards and Travel, Ross sits down with David C. Barnett, host of Small Business and Deal Making, to talk about one of the most overlooked opportunities for small business owners, using everyday business spending to earn credit card points, reduce tax burden, and fund luxury travel. David brings a unique perspective as a former American Express rep who spent years helping business owners and CFOs build corporate card strategies. Together, he and Ross break down the real math behind the 3% vendor fee, how to run a vendor analysis to find where cards are already accepted, why float can function like interest-free operating capital, and how accepting every form of payment actually becomes a competitive advantage. Credit Card Resources: ⁠5 Step Roadmap⁠ to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Best Credit Cards for Travel Melio: Pay vendors who don't take card with credit card to earn more points David’s Social Media: Instagram Website YouTube Itinerary Boss Socials: ⁠LinkedIn⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.   Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

    47 min
  3. Jun 3

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

    (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's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired. In episode 152 of Points, Cards and Travel, Ross joins Mary Ellen and Jo from Wonderland on Points to break down one of the most overlooked areas in the points and miles world — real estate and home spending. If you own a home, manage rental properties, or are about to furnish a new space, this episode shows you exactly how to turn those expenses into serious travel rewards. Ross walks through his personal property portfolio, the strategies he uses to separate business and personal spend, and how tools like Plastiq make it possible to earn points even when contractors only take cash. They also dig into the Mesa card and why homeowners finally have a way to earn points on mortgage payments, Costco purchases, and home renovation projects. Credit Card Resources: ⁠5 Step Roadmap⁠ to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Best Credit Cards for Travel Melio: Pay vendors who don't take card with credit card to earn more points Wonderland On Points Social Media: Instagram Apple Podcast Spotify Podcast Itinerary Boss Socials: ⁠LinkedIn⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.   Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

    51 min
  4. May 27

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

    (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's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired. In episode 151 of Points, Cards and Travel with Itinerary Boss, we break down the best credit cards for everyday spending and how to maximize points on dining, groceries, and shopping without overcomplicating your strategy. If you’ve ever wondered how to turn routine purchases into real travel rewards, this episode gives you a clear starting point. You’ll learn how to build a simple two-card strategy, when to use cash back cards versus transferable points, and how stacking the right cards can unlock significantly more value. We also walk through beginner-friendly options with no annual fee, mid-tier travel cards, and premium strategies like using Rakuten to multiply your earning potential. Whether you’re just getting started or looking to optimize your current setup, this episode shows how to maximize points on everyday spending and turn them into meaningful travel. Credit Card Resources: ⁠5 Step Roadmap⁠ to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Best Credit Cards for Travel Melio: Pay vendors who don't take card with credit card to earn more points Itinerary Boss Socials: ⁠LinkedIn⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.   Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

    18 min
  5. May 20

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

    (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's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired. In episode 150 of Points, Cards and Travel, Ross Alcorn joins DeAndre Coke to break down how he turned everyday spending into nearly $20,000 in luxury travel using a simple, strategic approach to points and miles. If you’ve ever wondered how to maximize points and miles without overcomplicating your setup, this episode gives you a clear roadmap built on real results. Discover how Ross leveraged business expenses, group travel planning, and credit card strategy to fund business class flights, high-end hotels, and an unforgettable honeymoon experience. They dive into practical ways to earn points faster, avoid common mistakes, and use tools like loyalty programs, transferable points, and welcome bonuses to unlock outsized value. You’ll also learn how to approach real estate spending, vendor payments, and large life events like weddings as opportunities to accelerate rewards. Credit Card Resources: ⁠5 Step Roadmap⁠ to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Best Credit Cards for Travel Melio: Pay vendors who don't take card with credit card to earn more points DeAndre’s Social Media: Instagram LinkedIn Itinerary Boss Socials: ⁠LinkedIn⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.   Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

    50 min
  6. May 13

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

    (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's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired. In episode 149 of Points, Cards and Travel, Ross sits down with Max Craig, also known as Points The Max, to break down the Southwest Companion Pass and how to use it to unlock massive travel value. If you’ve ever wondered how to turn one flight into two using points and miles, this episode gives you a clear and simple strategy to make it happen. Join us as we dive into how the Southwest Companion Pass works, who it makes sense for, and how to earn it using credit card points and smart timing. You’ll learn how to maximize points and miles through sign up bonuses, avoid common mistakes like poor timing, and build a long-term travel strategy that actually fits your lifestyle. We also cover repositioning flights, domestic travel planning, and how to combine Southwest with transferable points for bigger international trips. Credit Card Resources: ⁠5 Step Roadmap⁠ to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Best Credit Cards for Travel Melio: Pay vendors who don't take card with credit card to earn more points Max’s Social Media:InstagramFacebookWebsite Itinerary Boss Socials: ⁠LinkedIn⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.   Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

    50 min
  7. May 6

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

    (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's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired. In episode 148 of Points, Cards and Travel, we break down the most common beginner credit card mistakes that quietly cost you thousands in travel rewards. If you’ve ever redeemed points for gift cards or picked the wrong card, this episode will help you fix those errors and start maximizing points and miles the right way. Join us as we walk through 9 key mistakes that beginners make when getting started with credit card points, from missing welcome bonuses to using the wrong card for everyday spending. You’ll learn how to align your card strategy with your actual spending habits, avoid interest charges that erase your rewards, and why transfer partners are the key to unlocking premium travel. We also cover when to use travel portals, when to book direct, and how to turn simple spending into high-value rewards. If you want to maximize points and miles without overcomplicating your setup, this episode gives you a clear path forward. Subscribe for more strategies to travel better and get more value from every dollar. Credit Card Resources: ⁠5 Step Roadmap⁠ to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Best Credit Cards for Travel Melio: Pay vendors who don't take card with credit card to earn more points Itinerary Boss Socials: ⁠LinkedIn⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.   Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

    14 min
  8. Apr 29

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

    (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's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired. In episode 147 of Points, Cards and Travel, Ross sat down with Spencer Reese of Military Money Manual to break down how to turn everyday spending into powerful travel rewards using credit card points and smart business strategies. If you are a small business owner or in the military, this episode shows how to maximize points and miles without overcomplicating your setup while avoiding common mistakes that cost people thousands in missed travel value. Discover how credit card points can unlock business class flights, luxury hotels, and unforgettable trips worth thousands of dollars. We cover how to build a simple card strategy, why transferring points beats cash back, and how to leverage business expenses, welcome bonuses, and even large payments like taxes or rent to accelerate your rewards. From earning your first points to planning a $19,000 honeymoon almost entirely on points, this episode gives you a clear framework to travel better for less. Subscribe for more strategies to travel smarter and get more value from every dollar. Credit Card Resources: ⁠5 Step Roadmap⁠ to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Best Credit Cards for Travel Melio: Pay vendors who don't take card with credit card to earn more points Spencer's Social Media: Instagram YouTube Itinerary Boss Socials: ⁠LinkedIn⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.   Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

    51 min
5
out of 5
21 Ratings

About

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.

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