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
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How to Maximize Points on Everyday Spending: Best Credit Cards for Groceries, Dining, and Travel Rewards Explained
4d ago00:17:50Tap 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
2w ago00:49:46Tap 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
3w ago00:49:44Tap 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.
Transcribe →9 Credit Card Mistakes Beginners Make That Kill Points Value and How to Turn Them Into Free Travel
4w ago00:14:02Tap 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 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 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 Turn Business Spending into Free Travel: Credit Card Points, Miles, and Smart Strategies for Military Members and Entrepreneurs
Apr 2900:50:58Tap 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 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 ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsSpencer's Social Media:InstagramYouTubeItinerary 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 Danny Safran Turned Credit Card Points Into Family Trips, Luxury Hotels, and Europe Getaways Without Working in Travel
Apr 2200:41:39Tap 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 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 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 →The Power of Welcome Offers: How To Earn More Points, Avoid Bad Redemptions, and Turn Everyday Spend Into Luxury Travel
Apr 1500:24:40Tap 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 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 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 →The Hardest Part of Points Travel: Finding Award Availability with Kyle Potter from Thrifty Traveler
Apr 800:47:53Tap 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 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 ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsKyle’s Social Media:LinkedInItinerary 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 →Zero Percent Business Funding: How Entrepreneurs Use Credit Strategy, Higher Limits, and Smart Banking to Grow Without High Interest Debt
Apr 100:35:29Tap 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 143 of Points, Cards and Travel, Ross Alcorn sits down with Michael Boly to break down how business owners can use a smarter business credit strategy to unlock 0% interest funding, access higher credit limits, and avoid expensive debt. If you have ever wondered how entrepreneurs use credit cards to create flexibility, improve cash flow, and still position themselves for premium rewards, this episode gives you the foundation first. Michael explains the biggest mistakes business owners make before applying, including high utilization, weak personal credit foundations, and low-limit personal cards that quietly cap future approvals. The conversation also covers how 0% interest funding really works, why banks approve these offers, and how business owners can use them responsibly for marketing, growth, renovations, and major expenses without relying on traditional loans. They also discuss balance transfers, personal guarantees, long-term banking relationships, and why better credit structure creates better opportunities.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 pointsMichael’s Social Media:LinkedInItinerary 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 Hidden Strategy Behind Business Credit Cards: Use Spending, Billing Cycles, and Points to Unlock Travel and Business Flexibility
Mar 2500:43:42Tap 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 142 of World Travel Made Easy With Itinerary Boss, Ross Alcorn sits down with business expert David Barnett to break down how business credit card strategy can unlock travel rewards, improve cash flow, and create hidden financial advantages many entrepreneurs overlook.David spent years inside the American Express corporate card division and now helps people buy and sell businesses. In this conversation, he explains why most entrepreneurs think too small when it comes to business spending and credit cards. Instead of simply collecting points randomly, David shares how intentional planning can turn everyday expenses into meaningful travel rewards while also improving operating capital.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:YouTubeWebsiteItinerary 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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