Podcast
Points, Cards and Travel
Hosted by Ross Alcorn · EN
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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Episodes
Newest firstAll episodes
Transfer Partners vs. the Portal: How Ross Turned 200,000 Capital One Points Into an $11,350 Business Class Trip to Bangkok
5d ago00:13:46Tap to summarize(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 158 of Points, Cards and Travel, Ross continues the Points and Miles credit card series by breaking down exactly how to turn transferable points into business class flights instead of cash. He compares booking through the Capital One travel portal, where cards like the Venture Rewards and Venture X earn 5x to 10x points on flights, hotels, and rental cars, against transferring points directly to airline loyalty programs for outsized value. Using real examples from his own bookings. Ross shows how 200,000 Capital One points became two business class seats from Charlotte and Atlanta to Bangkok worth over $11,350 through British Airways and the Oneworld alliance, how 12,000 miles covered a $250 flight to Northern Virginia on Etihad, and how transfer bonuses from Qantas and British Airways turned smaller point balances into hundreds of dollars in savings on flights to Ohio and Grand Cayman. He also revisits the cardinal rules from last week's episode: never redeem for gift cards, cash, or statement credit, and never transfer points speculatively without confirming seat availability first. Credit Card Resources:5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsItinerary Boss Socials:LinkedInInstagramPinterestFacebook 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.
Transcribe →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
2w ago00:45:04Tap to summarize(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 157 of Points, Cards and Travel, Ross sits down with Ben from Ben's Big Deals to go deep on everything about hotels: the strategies, the mistakes, and the redemptions that actually move the needle. Ben got his start as a business traveler discovering La Quinta Inn loyalty perks, a "vacation" his wife was not impressed by, and that early lesson shapes everything he teaches today. They cover why emailing a property before you arrive (and telling them why you're there) can unlock complimentary upgrades, why talking to a manager beats the front desk, and why shorter stays make upgrades easier to land. Ben breaks down his points pyramid (bank points, then airlines, then hotels), why Hyatt and Accor are the exceptions to weak hotel point values, and why the Hilton free night certificate might be the single most valuable certificate in travel. They also get into aspirational stays worth chasing on points, including Alila Ventana in Big Sur and Hyatt's wellness brand Miraval, soon opening its first international property on the Red Sea. Ben closes with what's inside his Hotel Masterclass. Credit Card Resources:5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsBen’s Social Media:LinkedInWebsiteItinerary Boss Socials:LinkedInInstagramPinterestFacebook 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.
Transcribe →How to Plan a Stress-Free Trip: Flight Alerts, Travel Apps, and the Documents You Can't Afford to Forget
3w ago00:22:04Tap to summarize(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 156 of Points, Cards and Travel, Ross walks through the ultimate pre-trip planning and vacation document checklist, the exact system he's refined over 10+ years of travel mistakes so you don't have to repeat them. Before diving into documents, Ross covers the planning fundamentals: figuring out your travel style, setting up flight alerts through Google Flights, Skyscanner, or the Capital One travel portal, and choosing the right apps to manage your itinerary (Google Docs, Google Maps, TripIt, Viator, and more). From there, he breaks down the full document checklist for any trip, domestic or international, including visas and vaccinations, backup flight and accommodation confirmations, travel insurance (and which credit card benefits actually cover it), car rental and tour ticket downloads, emergency contacts, and passport copies. Ross also shares his cash and currency strategy for avoiding hidden transaction fees abroad, plus why splitting your cards, cash, and IDs across bags can save a trip when something goes wrong. If you want all of this compiled for you, Ross's free Stress-Free Travel Starter Kit has the entire checklist ready to go. Next week: the vacation packing checklist.Credit Card Resources:5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsItinerary Boss Socials:LinkedInInstagramPinterestFacebook 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.
Transcribe →How Business Owners Turn Everyday Expenses Into Free Family Vacations
4w ago00:49:22Tap to summarize(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, Ross sits down with Leslie Douglas, VP of Sales at Sell Better, sales trainer, podcast host, and self-described "Delta girly and Marriott girly." Leslie shares how she balances life on the road (30-40% travel) as a mom while building a points strategy that's covered nearly free trips, including an $80 all-in trip to New York with her daughter. The conversation dives into business expense strategies, including Leslie's story of putting a $10,000 car down payment on her American Express card for instant elite status, why every reimbursable expense should go on your personal card, and how recurring business costs can be converted into travel rewards. They also cover tools like Card Pointers Pro and Rakuten for stacking offers, the importance of picking an airline/hotel "home base," and simple money habits like automated high-yield savings accounts for funding future trips. Whether you're a sales rep, business owner, or frequent traveler with kids, this episode is packed with practical, real-world strategies for traveling more without spending more. Credit Card Resources:5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsLeslie’s Social Media:LinkedInInstagramItinerary Boss Socials:LinkedInInstagramPinterestFacebook 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.
Transcribe →The $580,000 Mistake That's Quietly Draining Business Owners' Travel Budgets
Jun 1700:15:52Tap to summarize(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 ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsItinerary Boss Socials:LinkedInInstagramPinterestFacebook 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.
Transcribe →Why Your Business Should Accept Every Form of Payment and How to Use That Spend to Fund Your Next Trip With David C. Barnett
Jun 1000:47:07Tap to summarize(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 ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsDavid’s Social Media:InstagramWebsiteYouTubeItinerary Boss Socials:LinkedInInstagramPinterestFacebook 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.
Transcribe →How Homeowners and Landlords Can Earn Massive Points on Real Estate, Renovations, Contractors, and Mortgage Payments With Ross Alcorn
Jun 300:51:23Tap to summarize(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 ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsWonderland On Points Social Media:InstagramApple PodcastSpotify PodcastItinerary Boss Socials:LinkedInInstagramPinterestFacebook 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.
Transcribe →How to Maximize Points on Everyday Spending: Best Credit Cards for Groceries, Dining, and Travel Rewards Explained
May 2700:17:50Tap to summarize(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 ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsItinerary Boss Socials:LinkedInInstagramPinterestFacebook 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.
Transcribe →How We Used Points To Save Over $19,000 On Our Honeymoon To Thailand and Bali
May 2000:49:46Tap to summarize(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 ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsDeAndre’s Social Media:InstagramLinkedInItinerary Boss Socials:LinkedInInstagramPinterestFacebook 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.
Transcribe →How to Unlock Unlimited 2-for-1 Flights with Southwest Companion Pass Using Points, Credit Cards, and Simple Planning
May 1300:49:44Tap to summarize(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 ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsMax’s Social Media:InstagramFacebookWebsiteItinerary Boss Socials:LinkedInInstagramPinterestFacebook 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.
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