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(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:
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.
(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:
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.
(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.
(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:
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.
(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.
(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.
(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:
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.
(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 146 of Points, Cards and Travel, Ross sits down with Danny Safran to break down how points and miles can create better family travel without needing a job in the travel industry. If you have ever wondered how to actually use points and miles in real life, this episode shows what it looks like to start small, stay consistent, and turn everyday spending into trips that feel bigger, easier, and far more affordable.
Danny shares how one Hilton card sparked a full points and miles strategy that led to long weekend getaways, luxury stays, Europe travel, family vacations, and unforgettable sports trips. You will hear why beginners should not rush, how to avoid missing a sign up bonus, how hotel status can unlock more value, and why planning family travel well in advance changes everything. This conversation also covers Hyatt Globalist benefits, free night certificates, Rakuten, travel planning, and using rewards for the trips that matter most. Subscribe for more practical points and miles strategies that help you travel better for less.
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.
(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 145 of Points, Cards and Travel, Ross breaks down how welcome offers can become one of the fastest ways to unlock better trips without increasing your travel budget. If you have ever wondered how people turn everyday spending into business class flights, luxury Hyatt stays, or free hotel nights, this episode explains the strategy in a simple, practical way. Ross walks through what welcome offers are, how minimum spend works, and why redemption value matters if you want to get real results from your points.
Ross also shares real examples of using welcome offers for a honeymoon to Bali and Thailand, Hyatt redemptions, IHG free nights, and a British Airways booking made even better with transfer bonuses. Along the way, he explains how business owners can think strategically about higher-spend bonuses, why transferable points matter, and what mistakes to avoid if you want more value from your points and miles. If you want a smarter credit card strategy that leads to better travel, this episode gives you a strong starting point.
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.
(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 144 of World Travel Made Easy, Ross Alcorn sits down with Kyle Potter from Thrifty Traveler to break down the biggest challenge in award travel today—finding award flights and business class availability before they disappear.
As points and miles become more popular, airlines are releasing fewer premium seats to partners and using more dynamic pricing. Kyle explains how tools, alerts, and smarter strategies can help travelers still unlock incredible deals like business class flights to Asia, Europe, and the Caribbean using points. If you've ever struggled to find award flights despite having plenty of points, this episode will completely change how you approach travel planning.
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
Kyle’s Social Media:
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.
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