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Points, Cards and Travel

Podcast door Ross Alcorn

Engels

Cultuur & Vrije Tijd

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Over Points, Cards and Travel

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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153 afleveringen

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

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 [https://yourbestcreditcards.com/?ccid=2015]. 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 [https://itineraryboss.kit.com/the-5-step-roadmap-to-your-next-free-5-star-luxury-vacation-the-1-card-that-gets-you-there?utm_source=ig&utm_medium=social&utm_content=link_in_bio&fbclid=PAZXh0bgNhZW0CMTEAc3J0YwZhcHBfaWQMMjU2MjgxMDQwNTU4AAGnsnF8N-YlYgYUH_EhRJC7AwZ0aIH70M1qm5JXFVv-gCqdXroCyTW31OtKPMs_aem_bpWd4IdukfBTmp39vl9hmg] Best Credit Cards for Travel [https://yourbestcreditcards.com/?ccid=2015] Melio [https://affiliates.meliopayments.com/f5l0dow7na3w]: Pay vendors who don't take card with credit card to earn more points Itinerary Boss Socials: ⁠LinkedIn⁠ [https://www.linkedin.com/in/rossalcornru/] ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ [https://www.instagram.com/itineraryboss/] ⁠⁠⁠⁠ [https://www.instagram.com/itineraryboss/]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.pinterest.com/itineraryboss/]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.tiktok.com/@itineraryboss?_t=8jUaFIFrI0R&_r=1] ⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.facebook.com/share/g/kg9fQpBYdDq3nAW8/?mibextid=K35XfP] ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.youtube.com/@ItineraryBoss]  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.youtube.com/@ItineraryBoss]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.

27 mei 2026 - 17 min
aflevering How We Used Points To Save Over $19,000 On Our Honeymoon To Thailand and Bali artwork

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 [https://yourbestcreditcards.com/?ccid=2015]. 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 [https://itineraryboss.kit.com/the-5-step-roadmap-to-your-next-free-5-star-luxury-vacation-the-1-card-that-gets-you-there?utm_source=ig&utm_medium=social&utm_content=link_in_bio&fbclid=PAZXh0bgNhZW0CMTEAc3J0YwZhcHBfaWQMMjU2MjgxMDQwNTU4AAGnsnF8N-YlYgYUH_EhRJC7AwZ0aIH70M1qm5JXFVv-gCqdXroCyTW31OtKPMs_aem_bpWd4IdukfBTmp39vl9hmg] Best Credit Cards for Travel [https://yourbestcreditcards.com/?ccid=2015] Melio [https://affiliates.meliopayments.com/f5l0dow7na3w]: Pay vendors who don't take card with credit card to earn more points DeAndre’s Social Media: Instagram [https://www.instagram.com/deandre.coke/] LinkedIn [https://www.linkedin.com/in/deandrecoke/] Itinerary Boss Socials: ⁠LinkedIn⁠ [https://www.linkedin.com/in/rossalcornru/] ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ [https://www.instagram.com/itineraryboss/] ⁠⁠⁠⁠ [https://www.instagram.com/itineraryboss/]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.pinterest.com/itineraryboss/]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.tiktok.com/@itineraryboss?_t=8jUaFIFrI0R&_r=1] ⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.facebook.com/share/g/kg9fQpBYdDq3nAW8/?mibextid=K35XfP] ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.youtube.com/@ItineraryBoss]  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.youtube.com/@ItineraryBoss]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.

20 mei 2026 - 49 min
aflevering How to Unlock Unlimited 2-for-1 Flights with Southwest Companion Pass Using Points, Credit Cards, and Simple Planning artwork

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 [https://yourbestcreditcards.com/?ccid=2015]. 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 [https://itineraryboss.kit.com/the-5-step-roadmap-to-your-next-free-5-star-luxury-vacation-the-1-card-that-gets-you-there?utm_source=ig&utm_medium=social&utm_content=link_in_bio&fbclid=PAZXh0bgNhZW0CMTEAc3J0YwZhcHBfaWQMMjU2MjgxMDQwNTU4AAGnsnF8N-YlYgYUH_EhRJC7AwZ0aIH70M1qm5JXFVv-gCqdXroCyTW31OtKPMs_aem_bpWd4IdukfBTmp39vl9hmg] Best Credit Cards for Travel [https://yourbestcreditcards.com/?ccid=2015] Melio [https://affiliates.meliopayments.com/f5l0dow7na3w]: Pay vendors who don't take card with credit card to earn more points Max’s Social Media:Instagram [https://www.instagram.com/points.to.the.max/]Facebook [https://www.facebook.com/MilesMentorMax/]Website [https://www.pointstothemax.com/⁠] Itinerary Boss Socials: ⁠LinkedIn⁠ [https://www.linkedin.com/in/rossalcornru/] ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ [https://www.instagram.com/itineraryboss/] ⁠⁠⁠⁠ [https://www.instagram.com/itineraryboss/]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.pinterest.com/itineraryboss/]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.tiktok.com/@itineraryboss?_t=8jUaFIFrI0R&_r=1] ⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.facebook.com/share/g/kg9fQpBYdDq3nAW8/?mibextid=K35XfP] ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.youtube.com/@ItineraryBoss]  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.youtube.com/@ItineraryBoss]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.

13 mei 2026 - 49 min
aflevering 9 Credit Card Mistakes Beginners Make That Kill Points Value and How to Turn Them Into Free Travel artwork

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 [https://yourbestcreditcards.com/?ccid=2015]. 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 [https://itineraryboss.kit.com/the-5-step-roadmap-to-your-next-free-5-star-luxury-vacation-the-1-card-that-gets-you-there?utm_source=ig&utm_medium=social&utm_content=link_in_bio&fbclid=PAZXh0bgNhZW0CMTEAc3J0YwZhcHBfaWQMMjU2MjgxMDQwNTU4AAGnsnF8N-YlYgYUH_EhRJC7AwZ0aIH70M1qm5JXFVv-gCqdXroCyTW31OtKPMs_aem_bpWd4IdukfBTmp39vl9hmg] Best Credit Cards for Travel [https://yourbestcreditcards.com/?ccid=2015] Melio [https://affiliates.meliopayments.com/f5l0dow7na3w]: Pay vendors who don't take card with credit card to earn more points Itinerary Boss Socials: ⁠LinkedIn⁠ [https://www.linkedin.com/in/rossalcornru/] ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ [https://www.instagram.com/itineraryboss/] ⁠⁠⁠⁠ [https://www.instagram.com/itineraryboss/]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.pinterest.com/itineraryboss/]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.tiktok.com/@itineraryboss?_t=8jUaFIFrI0R&_r=1] ⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.facebook.com/share/g/kg9fQpBYdDq3nAW8/?mibextid=K35XfP] ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.youtube.com/@ItineraryBoss]  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.youtube.com/@ItineraryBoss]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.

6 mei 2026 - 14 min
aflevering How to Turn Business Spending into Free Travel: Credit Card Points, Miles, and Smart Strategies for Military Members and Entrepreneurs artwork

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 [https://yourbestcreditcards.com/?ccid=2015]. 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 [https://itineraryboss.kit.com/the-5-step-roadmap-to-your-next-free-5-star-luxury-vacation-the-1-card-that-gets-you-there?utm_source=ig&utm_medium=social&utm_content=link_in_bio&fbclid=PAZXh0bgNhZW0CMTEAc3J0YwZhcHBfaWQMMjU2MjgxMDQwNTU4AAGnsnF8N-YlYgYUH_EhRJC7AwZ0aIH70M1qm5JXFVv-gCqdXroCyTW31OtKPMs_aem_bpWd4IdukfBTmp39vl9hmg] Best Credit Cards for Travel [https://yourbestcreditcards.com/?ccid=2015] Melio [https://affiliates.meliopayments.com/f5l0dow7na3w]: Pay vendors who don't take card with credit card to earn more points Spencer's Social Media: Instagram [https://www.instagram.com/militarymoneymanual/] YouTube [https://www.youtube.com/@MilitaryMoneyManual] Itinerary Boss Socials: ⁠LinkedIn⁠ [https://www.linkedin.com/in/rossalcornru/] ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ [https://www.instagram.com/itineraryboss/] ⁠⁠⁠⁠ [https://www.instagram.com/itineraryboss/]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.pinterest.com/itineraryboss/]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.tiktok.com/@itineraryboss?_t=8jUaFIFrI0R&_r=1] ⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.facebook.com/share/g/kg9fQpBYdDq3nAW8/?mibextid=K35XfP] ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.youtube.com/@ItineraryBoss]  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.youtube.com/@ItineraryBoss]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.

29 apr 2026 - 50 min
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