Explore every episode of the podcast Points, Cards and Travel
| Title | Pub. Date | Duration | |
|---|---|---|---|
| How Danny Safran Turned Credit Card Points Into Family Trips, Luxury Hotels, and Europe Getaways Without Working in Travel | 22 Apr 2026 | 00:41:39 | |
(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 Melio: Pay vendors who don't take card with credit card to earn more points Itinerary Boss Socials: Pinterest 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. | |||
| The Power of Welcome Offers: How To Earn More Points, Avoid Bad Redemptions, and Turn Everyday Spend Into Luxury Travel | 15 Apr 2026 | 00:24:40 | |
(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 Melio: Pay vendors who don't take card with credit card to earn more points Itinerary Boss Socials: Pinterest 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. | |||
| The Hardest Part of Points Travel: Finding Award Availability with Kyle Potter from Thrifty Traveler | 08 Apr 2026 | 00:47:53 | |
(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 Melio: Pay vendors who don't take card with credit card to earn more points Kyle’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Zero Percent Business Funding: How Entrepreneurs Use Credit Strategy, Higher Limits, and Smart Banking to Grow Without High Interest Debt | 01 Apr 2026 | 00:35:29 | |
(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 There Melio: Pay vendors who don't take card with credit card to earn more points Michael’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| The Hidden Strategy Behind Business Credit Cards: Use Spending, Billing Cycles, and Points to Unlock Travel and Business Flexibility | 25 Mar 2026 | 00:43:42 | |
(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 There Melio: Pay vendors who don't take card with credit card to earn more points David’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| How Business Owners Use 0% Interest Credit Cards to Invest in Growth, Reduce Financial Stress, and Earn Travel Points Along the Way | 18 Mar 2026 | 00:31:34 | |
(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 141 of World Travel Made Easy With Itinerary Boss, Ross Alcorn sits down with stand-up comedian and business owner Scott Bedgood to discuss how entrepreneurs can use credit cards strategically to grow their business without taking on traditional loans. Scott shares how discovering 0% interest credit cards changed the way he invests in his speaking and coaching business. Instead of feeling pressured to generate immediate revenue after every expense, he now has the flexibility to make smart investments that support long-term growth. Ross also explains how points and miles strategy allows business owners to earn valuable travel rewards from expenses they already have. Credit Card Resources: 5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Melio: Pay vendors who don't take card with credit card to earn more points Scott’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| From One Card to Luxury Travel: How Smart Points Strategy Saved $4,000 on a Honeymoon | 11 Mar 2026 | 00:30:24 | |
(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 140 of World Travel Made Easy With Itinerary Boss, Ross Alcorn welcomes back Lauren Perussault to break down how a simple Points, Cards and Travel strategy turned everyday spending into a luxury honeymoon experience. After years of researching credit cards and feeling overwhelmed by options, Lauren finally implemented a clear strategy that helped her unlock thousands in travel value. By strategically opening the right credit cards before major wedding expenses, Lauren and her husband earned welcome bonuses that covered flights and significantly reduced the cost of their St. Lucia honeymoon. Using a combination of Chase points, Capital One points, and travel portal boosts, they saved over $4,000 on flights and a five star resort stay. The episode dives into how beginners can start building a Points, Cards and Travel system without spreadsheets or analysis paralysis. Ross and Lauren also discuss stacking benefits like airport lounge access, travel credits, and strategic card usage to maximize value from everyday spending. Credit Card Resources: 5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Melio: Pay vendors who don't take card with credit card to earn more points Lauren’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Your First Female Solo Trip Blueprint: Safety Tips, Travel Trends, Travel Insurance, and Points Strategy with Henah Velez | 04 Mar 2026 | 00:29:56 | |
(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 140 of Points, Cards, and Travel, Ross Alcorn welcomes back Henah Velez to share solo female travel tips that help you feel safer, calmer, and more present on every trip. Join us as we break down travel trends 2026 listeners are already noticing, like digital detox travel, analog getaways, and choosing slower destinations over crowded viral hotspots. Henah shares solo female travel tips you can use immediately, including picking a safer location first, sharing your live location with someone you trust, reading reviews through a solo traveler lens, and arriving during daylight when possible. She also explains how to ease into your first solo trip with solo dates, short weekend test runs, and low pressure ways to meet people like walking tours and silent book clubs. Plus, we talk points and miles strategies that support safety and comfort, including flexible points, hotel credits, and why the Chase Sapphire Preferred is a strong beginner card. We close with a must do reminder on travel insurance and why Squaremouth can be worth it. Credit Card Resources: 5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Melio: Pay vendors who don't take card with credit card to earn more points Henah’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| How she saved $4,000 on a United Kingdom and Ireland Trip Using Points: Transfer Partners, Sweet Spots, and Smarter Booking Tips with Lauren Ross | 25 Feb 2026 | 00:33:03 | |
(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 138 of Points, Cards, and Travel, Ross sits down with Lauren Ross to show how a simple credit card strategy can turn everyday spending into real travel. Discover how Lauren went from booking only through portals to confidently using points for flights, hotels, and high value perks, without making it a second job. Lauren breaks down her exact credit card strategy using Chase Ultimate Rewards, Amex Platinum benefits, and Hyatt points to cover a luxury stay in Dublin and book United premium economy home through Air Canada Aeroplan. You’ll hear how to evaluate “good deals,” why airline alliances matter, and when it is smarter to book directly instead of relying on a travel portal. She also shares how Amex Fine Hotels and Resorts credits can stack free breakfast and on property perks to cut cash costs fast. If you want a credit card strategy that feels attainable and repeatable, this episode is your roadmap. Credit Card Resources: 5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Melio: Pay vendors who don't take card with credit card to earn more points Lauren’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| BILT 2.0 Rewards Explained: How to use Rent and Mortgage Payments to fund free travel with Henah Velez | 18 Feb 2026 | 00:25:56 | |
(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 137 of Points, Cards, and Travel, join us as Ross Alcorn sits down with Henah Velez to make the BILT Card feel simple again. If you have rent or a mortgage and you want travel rewards without adding more complexity, this episode breaks down what matters, what changed, and how to think through it without getting stuck in the math. Henah shares how she originally got the Built Card as a renter paying around $4,000 in rent, why earning something beats earning nothing, and how she uses BILT points to book trips like Atlanta to Europe on Flying Blue promos, plus a 4.5K Alaska redemption that replaced a $400 cash ticket. They also unpack housing only vs BILT cash, how transaction fees really work, and why using a calculator can save you from guessing. If you want a cleaner credit card strategy that matches your real spending, this is your roadmap. Credit Card Resources: 5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Melio: Pay vendors who don't take card with credit card to earn more points Henah’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| How Home Renovations With 0% APR Cards Funded a $6,000 Hawaii Trip on Points with Chris Reichenbach | 11 Feb 2026 | 00:32:37 | |
(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 136 of Points, Cards, and Travel, join us as Ross sits down with real estate investor Chris Reichenbach to show how points and miles can fund real travel while helping you move faster in business. If you are paying renovation costs by check or ACH, you might be missing a safer, more flexible way to pay, earn rewards, and keep projects moving. Chris shares how he went from fearing credit cards to using 0% APR business credit cards to cover materials, float expenses between hard money draws, and rack up points and miles without chasing random offers. You will hear how he handled a nightmare renovation that jumped to $140,000, why contractor payment methods matter, and how credit cards can protect you when work is not delivered. He also breaks down how he used points and miles to book a Hawaii trip that saved over $6,000 and created a life moment he will never forget. Credit Card Resources: 5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Melio: Pay vendors who don't take card with credit card to earn more points Chris’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| How to Earn Maximum Credit Card Points, Hotel Room Block Rewards, and Plan a Stress-Free Destination Wedding with Kerry Krull (The Wedding App) | 04 Feb 2026 | 00:27:35 | |
(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 135 of World Travel Made Easy With Itinerary Boss, Ross sits down with Kerry Krull, founder of The Wedding App, to break down what actually makes destination weddings stressful and how couples can avoid it. Most destination weddings don’t fall apart because of travel costs or venues. They fail because guests don’t know what’s going on. Join us as Kerry shares insights from her background in corporate events and wedding planning, explaining why destination weddings should be treated like multi-day experiences, not just a single ceremony. From missed welcome parties to flight cancellations and last-minute schedule changes, Kerry explains how lack of communication creates chaos and how real-time updates can completely change the guest experience. Website: Credit Card Resources: The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Best Credit Cards for Travel Transfer Bonus Notifications Melio: Pay vendors who don't take card with credit card to earn more points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Kerry’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Why 40–50% of Flights Drop After Booking and How SkyKey Automatically Gets You the Difference Back with Jacob Goldberg, Co-Founder SkyKey | 28 Jan 2026 | 00:31:24 | |
(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 134 of World Travel Made Easy With Itinerary Boss, Ross sits down with Jacob Goldberg, co-founder of SkyKey, to break down one of the biggest hidden problems in airfare pricing and the simplest solution most travelers are missing. Airlines constantly change prices, and most travelers never check their ticket again after booking. Jacob explains why 40–50% of flights drop in price after purchase and how SkyKey monitors flights 24/7 to automatically secure refunds or flight credits when prices fall. With average savings of $130 per flight, SkyKey removes the stress of timing airfare purchases, deal alerts, and mental gymnastics especially for families, business travelers, and anyone booking peak travel dates. Website: Credit Card Resources: The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Best Credit Cards for Travel Transfer Bonus Notifications Melio: Pay vendors who don't take card with credit card to earn more points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Jacob’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Positioning Flights Explained: How to Unlock Business Class Awards From Any Airport with Hunter Threadgill from Professor of Points & Frequent Traveler University | 21 Jan 2026 | 00:37:26 | |
(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 133 of World Travel Made Easy With Itinerary Boss, Discover how positioning flights can turn “I don’t live near a hub” into real business-class options. Hunter Threadgill aka the Professor of Points breaks down what positioning flights are, why they work, and how to use them without blowing up your trip when delays happen. You’ll learn how to spot the best airports to position through (think Chicago, Boston, Seattle, Vancouver, and more), how to protect the long-haul seat you actually care about, and how to plan stress-free buffers especially when you’re on separate tickets or switching airports. Hunter also shares how he uses hotel points (like Hyatt and free-night certificates) to turn an overnight into a bonus vacation day, plus a simple way to think about fuel surcharges and smarter Europe gateways like Paris and Amsterdam. We also touch award availability patterns and why competition at “someone else’s hub” can create opportunities. Website: Credit Card Resources: The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Best Credit Cards for Travel Transfer Bonus Notifications Melio: Pay vendors who don't take card with credit card to earn more points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Hunter’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Simplify Tracking Your Points with AwardWallet: Reprice Flights & Avoiding Costly Mistakes With JT Genter of AwardWallet | 14 Jan 2026 | 00:39:47 | |
(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 132 of World Travel Made Easy With Itinerary Boss, Ross Alcorn sits down with JT Genter, Editor-in-Chief at AwardWallet, to break down how travelers can finally get organized with points and miles without spreadsheets, stress, or lost rewards. If you’ve ever forgotten expiration dates, redeemed points poorly, or felt overwhelmed managing multiple loyalty programs, this episode delivers clarity. Join us as JT shares how AwardWallet helps track credit card points, airline miles, hotel rewards, expiration alerts, and even flight repricing opportunities, all in one dashboard. You’ll hear how beginners can avoid analysis paralysis, how advanced travelers spot better redemptions, and why flexibility across programs leads to stronger value. JT also reveals common mistakes he sees, including why redeeming points for gift cards quietly destroys value. Website: Credit Card Resources: The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Best Credit Cards for Travel Transfer Bonus Notifications Melio: Pay vendors who don't take card with credit card to earn more points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! JT’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Credit Card Roadmapping Made Simple: Starter Cards, Premium Card Annual Fees, and Smarter Point Redemptions with Spencer Johnson | 07 Jan 2026 | 00:53:06 | |
(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 131 of World Travel Made Easy With Itinerary Boss, Ross Alcorn sits down with Spencer Johnson to break down how to build a simple, sustainable credit card strategy that actually leads to travel. Instead of chasing every shiny offer, Spencer explains how to start with the right foundation, choose cards that fit your real spending, and use transferable points to unlock better flights and hotels. This conversation covers annual fee math, welcome bonus timing, and why most people overcomplicate points and miles far too early. Spencer also explains how “cash back” cards can quietly become powerful travel tools, when diversification across banks actually helps, and how to avoid getting stuck with points you can’t use. If you want a clear roadmap whether you’re brand new or trying to clean up a messy setup, this episode delivers practical advice you can apply immediately. Subscribe to make sure you don’t miss future expert breakdowns. Website: Credit Card Resources: The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Melio: Pay vendors who don't take card with credit card to earn more points Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Spencer’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Southwest Companion Pass Explained: 135K Points Strategy, Companion Swap Rules, and Post-Change Reality with Max Craig (Points to the Max) | 31 Dec 2025 | 00:48:57 | |
(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 130 of World Travel Made Easy With Itinerary Boss, Ross sits down with Max Craig (“Points to the Max”) for a practical Southwest Companion Pass playbook that works in 2025 and 2026 without the timing mistakes that kill your value. Discover how the Southwest Companion Pass really works (true buy-one-get-one for just taxes and fees), why earning it early in the year can unlock up to 21+ months of upside, and how to approach the two-card method using P1/P2 strategy and the 24-month rules. Max also breaks down the recent Southwest changes, basic fare limits, fare multipliers, assigned seating, and bag fees and the simple math that can make a card’s annual fee pay for itself fast. You’ll also hear a smart repositioning flight framework (like Nashville → Chicago) to reach better international award deals, plus the most common Companion Pass pitfalls, spend tracker surprises, returns, and companion-change headaches (and why calling is often better). Website: Credit Card Resources:
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Max’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Active Duty Credit Cards Rewards: No Annual Fee's, Smart Card Sequencing & Credits to Build Wealth and Book Luxury Vacations with Spencer Reese | 23 Dec 2025 | 01:08:22 | |
(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 129 of World Travel Made Easy With Itinerary Boss, we dive into the world of military credit cards with Spencer Rees from Military Money Manual. If you’re active duty, Guard/Reserve, or a military spouse, this episode shows how fee-waived premium cards can unlock premium travel, elite hotel status, and thousands in yearly savings. Learn exactly how to confirm MLA eligibility, why Amex Platinum and Chase Sapphire Reserve are the heavy hitters, and how to avoid the most common mistakes service members make with points and miles. Join us as Spencer breaks down the Military Lending Act, reveals the difference between active duty and veteran benefits, and shares real stories of flying business class on PCS moves, stacking hotel status overseas, and converting unused credits into real-life wealth (including Roth IRA contributions). You’ll also learn simple systems for batching credits, tracking cards, protecting your credit score, and maximizing rewards without overwhelm. Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Spencer’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Simplify Finances First Before Credit Card Rewards: Banking Automation & High Yield Savings Foundation that Fuels Travel with Steve Domino | 17 Dec 2025 | 00:27:16 | |
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 128 of World Travel Made Easy With Itinerary Boss, Ross sits down with Steve Domino, co-founder of Crew, to show how a smart banking setup makes travel goals actually happen. Credit Card Points are only valuable when your money system is simple, automatic, and built to prevent overspending. Steve walks through Crew’s pockets, paycheck rules, joint accounts, and kid allowances so your bills, savings, and travel budget move themselves. Join us as we connect Credit Card Points strategy to real-life family finances: auto bill pay from a bills pocket, overspend protection tied to your budget, and a month-in-review that spotlights where to earn more. Crew offers a high-yield checking account (with Itinerary Boss code, a limited APY boost) and is building a smart charge card that pays down daily or weekly so you get rewards without carrying a balance. If you’ve tried tools like Greenlight, Monarch, or YNAB, Crew combines the pieces in one place for Points & Miles beginners and busy parents. Subscribe for more practical systems that help you travel more without debt. Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Steve’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Family Slow Travel and World Schooling: How Business Owners Can Use of Credit Card Points for Extended Europe Travel with Suzy May | 10 Dec 2025 | 00:43:21 | |
(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 127 of World Travel Made Easy With Itinerary Boss, Ross sits down with money coach and podcaster Suzy May to break down how world schooling really works for regular families. You’ll hear how her family splits time between Colorado and Spain, why world schooling isn’t just for digital nomad influencers, and how the cost of preschool at home can equal a full school year abroad. If you’ve ever wondered whether world schooling and slow family travel are only for the ultra-rich, this conversation will fix that fast. They dig into choosing locations, navigating visas like Schengen and Mexico’s 180-day rule, and comparing real numbers on daycare, private schools, and programs like international schools or world schooling hubs. Then they tie it all back to points and miles, how slow travel uses fewer flights, why positioning flights and trains matter, and how business owners can turn everyday spending into long-haul family trips. If you want your kids learning from the world instead of just worksheets, this episode will give you a clear, practical roadmap. Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Suzy’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Hotel Upgrades, Elite Status Secrets & Free Night Certificates: How to Turn Every Stay Into a VIP Experience With Ben’s Big Deals | 03 Dec 2025 | 00:45:38 | |
(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 126 of World Travel Made Easy With Itinerary Boss, we sit down with Ben from Ben’s Big Deals to break open the world of hotel upgrades and real-life elite status strategy. If you’ve ever wondered why some people always seem to snag better rooms, free nights, and special treatment, this hotel upgrade deep dive is your playbook. Ben shares how he went from La Quinta business trips to luxury stays using hotel upgrades, elite status, and smart use of free night certificates instead of just chasing flashy flights. You’ll learn why emailing the property before arrival matters, how ownership and brand relationships affect your stay, and when to pay cash vs. points. We get into IHG, Hyatt, Marriott, Hilton, best rate guarantees, elite status shortcuts, and how to think like a VIP guest without overcomplicating the game. If you want your next trip to feel like an intentional experience instead of a random hotel night, this is one you’ll want to replay and take notes on. Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Ben’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| How You Can Use Credit Cards To Reward Yourself Even If You Have Financial Trauma with Mariah Hudler | 26 Nov 2025 | 00:48:48 | |
(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 125 of World Travel Made Easy With Itinerary Boss, licensed mental health clinician Mariah Hudler unpacks the link between money mindset and travel freedom. Join us as we explore Points & Miles through the lens of financial therapy, identifying money scripts (avoidance, vigilance, status, worship), healing financial trauma, and building calm, repeatable systems that actually lead to more trips. Mariah shares practical steps: monthly money dates, values-based spending, clear goals, and vision boards that connect emotions to action. We discuss paying in full, automating savings, and aligning Points & Miles with your “rich life” priorities so award travel feels intentional, not impulsive. You’ll hear how couples can increase transparency, communicate better, and use Points & Miles to reward consistent habits. Expect simple frameworks you can use today, from transferring wisely to tracking net worth plus examples across Chase Ultimate Rewards, Capital One, and Southwest. Ready to become an “optionaire” and design travel that fits your life? Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Mariah’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Shopping Portals That Earn Free Points: Earn AMEX or Bilt Points and Turn Online Buys into Free Flights + Hotels | 20 Nov 2025 | 00:18:18 | |
(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 124 of World Travel Made Easy with Itinerary Boss, we revisit one of the most practical tutorials ever released on how to earn more from the shopping you already do. This replay dives back into shopping portals like Rakuten and SaveWise, showing how simple browser extensions can multiply your points and cash back with zero extra effort. You’ll learn how to link your American Express account to convert Rakuten cash back into Membership Rewards, how to stack SaveWise alerts for Amex, Chase, and SimplyMiles, and how these small tweaks can add up to free flights and upgraded stays. Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Itinerary Boss Socials: Pinterest 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. | |||
| The Hyatt Globalist Blueprint: 9x Earnings, Guest of Honor Perks, and $1,500 Luxury Nights for 45K Points | 19 Nov 2025 | 00:36:52 | |
(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 123 of World Travel Made Easy With Itinerary Boss, Ross sits down with Ali for a hands-on Hyatt deep dive. Join us as we unpack why Hyatt delivers outsized value in Points & Miles, from reliable award charts and a powerful Points Calendar to elite perks that actually show up at check-in. You’ll hear how Globalist benefits, suite upgrades, free breakfast, and waived resort fees combine with simple tactics like billing everything to the room for 9x to stretch every stay. We cover Points & Miles fundamentals most travelers miss: Chase and Bilt transfer partners for Hyatt, when to earn & burn, how to time off-peak redemptions, and smart scenarios for buying points (hello, Alila Ventana). Families get practical booking paths (Guest of Honor, points-plus-cash), and American Airlines flyers learn why linking accounts and status matching multiplies returns. If you’re choosing between Hyatt, Marriott, and Hilton, this conversation shows where the real cents-per-point value lives. Ready to plan Park Hyatt-level memories without Park Hyatt cash? Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Ali’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| The United Insider’s Guide — Air Canada Aeroplan Secrets, Hub Sweet Spots & Smarter Family Trips | 11 Nov 2025 | 00:29:31 | |
(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 122 of World Travel Made Easy With Itinerary Boss, Ross sits down with Matthew Dong (WuHoo Group LLC) to demystify Dulles (IAD) as a Star Alliance springboard. If you’ve ever asked why that United flight often prices cheaper with Air Canada Aeroplan or how to find saver awards without spending hours, this one’s for you. We cover Points & Miles basics that work today: partner booking, hub-to-hub domestic routes, real award comparisons (80k vs 60k vs 45k), and when to use tools like seats.aero. Join us as Mattew shares family travel tactics, what lap-infant fees really cost internationally, how Aeroplan shows seats left, and why Capital One Venture X plus Priority Pass lounges at IAD/DCA simplify airport days. You’ll learn how Points & Miles stretch further with transfer bonuses, why diversification matters across Amex/Chase/Capital One, and how to sanity-check award availability fast. Whether you’re eyeing Paris on Air France or a last-minute Turkish business class, this is a clear path from Dulles to “booked.” Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Matthew’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Alaska Atmos Program Deep Dive: Smarter Ways to Earn, Redeem, and Travel on Partner Airlines like American with Betsey Wilson | 05 Nov 2025 | 00:42:10 | |
(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 121 of World Travel Made Easy With Itinerary Boss, Ross sits down with Betsey Wilson, founder of Become Travel Rich, to decode how everyday travelers can use Alaska Airlines Atmos points for real value. If you fly from American hubs or you are new to Points & Miles, this is a clear blueprint to upgrade faster, spend less, and book trips that fit actual family calendars. Join us as Betsey breaks down practical redemptions like 4,500-point economy seats and 35,000-point lie-flats, how American elite benefits map on Alaska metal, why partner bookings matter, and when to pay cash versus use points. You will learn companion award differences, smart same-day change tactics, and why Condor is a standout partner for Europe and beyond. We also hit status-earning via non-airline partners and how to think about premium cards without fear of annual fees. If you want points to translate into better seats and better trips, this one’s for you. Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Betsey's Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| How to Leverage Business Expenses into First-Class Travel using Lifestyle Assets with CEO of Vodyssey, Shawn Moore | 29 Oct 2025 | 00:53:01 | |
(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 120 of World Travel Made Easy With Itinerary Boss, Ross sits down with Vodacy CEO Shawn Moore to unpack the real playbook behind lifestyle assets, short term rentals, and smarter travel. If you care about ROI and real memories, this one’s for you. Learn how to balance cash flow with appreciation, when to trade up, and why setup and furnishing matter more than most spreadsheets admit. You’ll also hear how to align your Itinerary with shoulder season for better rates and quieter trips. Shawn breaks down conservative investing habits, return on equity, and the four pillars of real estate returns, plus simple ways business owners and high W2 earners can use Credit Card Points without overextending. We also talk about tax advantages like bonus depreciation and how to protect time by outsourcing management. If you want to turn business spend into Credit Card Points and smarter Credit Card Points redemptions while building a travel-friendly portfolio, this is your roadmap. Discover how lifestyle assets support long term wealth and stress free travel. Subscribe. Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Shawn’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Tracking Credit Card Offers, Stack Rewards, and Automate Savings Using the CardPointers App with Brooke Merkle | 22 Oct 2025 | 00:34:17 | |
(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 119 of World Travel Made Easy With Itinerary Boss, we sit down with Brooke from CardPointers to show you how to turn everyday spending into real travel. If picking the right card at checkout feels confusing, CardPointers simplifies it so you earn more rewards with less effort. From the Best Card wizard to the browser extension that activates hundreds of bank offers in seconds, you will capture value you are probably leaving on the table. Discover how Autopilot on iPhone surfaces the best card on your lock screen as you shop, why profiles help families and teams earn smarter, and how stacking portal rewards with card offers multiplies points fast. We keep it beginner friendly while sharing power user strategies that respect YourBestCreditCards.com guidelines. If you want practical, repeatable systems for Travel rewards and Points & Miles, this one is packed with tips. Subscribe to never miss future episodes. Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Brooke’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| International Family Travel Best Practices: Spain, Japan, and Points Mistakes to Avoid with Alex Maiersperger | 15 Oct 2025 | 00:44:28 | |
(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 118 of World Travel Made Easy With Itinerary Boss, Ross sits down with Alex Maiersperger, global marketing lead at SAS, host of The Health Pulse podcast, and cofounder of the Young Health Leader Summit. Together, they explore the realities of traveling with kids, the mistakes families often make, and how to turn everyday expenses into memorable international trips. Join us as Alex shares how his family planned meaningful journeys to Japan and Spain, the lessons learned from navigating hotels in Europe with three kids, and why prioritizing family experiences matters more than work deadlines. You’ll also hear strategies for stretching your budget, avoiding common pitfalls like paying full price, and even creative lodging ideas like home exchanges. Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Alex’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| How E-Commerce Founders can use Business Spend to Earn Millions of Points and Travel for Free with MentorPass CEO Kenny Hanson | 08 Oct 2025 | 01:01:09 | |
(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 117 of World Travel Made Easy With Itinerary Boss, we dive into the inspiring journey of Kenny Hanson, founder and CEO of MentorPass. After six years at Accenture in Washington, DC, Kenny took a bold leap, moving to Bali to reset, recharge, and begin building a global mentorship platform. Join us as Kenny shares how travel reshaped his perspective, from lowering costs of living abroad to immersing in a community of creative entrepreneurs. He explains how those experiences influenced the foundation of MentorPass, which now connects founders and business owners with world class mentors who have built brands like Athletic Greens, Native, and Bloom Nutrition. Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Kenny's Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Optimizing High Business Credit Card Spend for Personal First Class and Five Star Luxury Vacations with Ryan Melnick | 01 Oct 2025 | 00:47:39 | |
(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 116 of World Travel Made Easy With Itinerary Boss, Ross sits down with Ryan Melnick, CEO of Category 5 Windows and founder of First Class Advisors. Ryan shares his journey from eBay flips and dropshipping to owning a construction business that now generates millions in spend, and how he transforms that spend into millions of points for premium travel. Ryan breaks down how business owners can rethink the “3% fee” myth, why paying vendors with credit cards can supercharge cash flow, and how smart use of programs like Chase, Amex, and Capital One unlocks first-class flights and luxury hotel stays. He also shares redemption stories, from sending family to London in Virgin Upper Class for 29,000 points to booking Singapore Airlines’ famous A380 double bed in the sky. Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Ryan’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Maldives Travel on Points and Miles: Overwater Villas, Hilton Aspire Free Nights, Fifth Night Free Math, and Smarter Positioning Flights with Carissa Rawson of Rove Miles | 24 Sep 2025 | 00:27:34 | |
(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 115 of World Travel Made Easy With Itinerary Boss, we dive into Maldives travel on points with Carissa Rawson, Director of Travel and Marketing at Rove and veteran points and miles expert. If you have dreamed of an overwater villa but worry about cost, this conversation breaks down a clear path using points and miles to get you there. Carissa shares why the Maldives keeps delivering wonder, then maps the real strategy: position to Doha, Dubai, or Europe for business class award space, buy a short hop to MLE, and use hotel programs where the value shines. We cover Hilton Aspire’s uncapped free night, fifth night free with Hilton and Marriott, Hyatt sweet spots, elite breakfast benefits, and how all inclusive vouchers can control food and drink costs. You will also learn when to choose Park Hyatt vs Waldorf Astoria, how to think about seaplane transfers, and what a realistic Maldives budget looks like once you arrive. Ready to turn your points into sunsets and snorkeling? Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Carissa’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Are Credit Card Points Taxable? Best Practices for Business Owners, Investors, and Side Hustlers with CPA Rachel Earl | 17 Sep 2025 | 00:53:22 | |
(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 114 of World Travel Made Easy With Itinerary Boss, CPA and points enthusiast Rachel Earl joins Ross to clear up the confusion around Credit Card Points and taxes for business owners, side hustlers, and real estate investors. From statement credits to partnership distributions, Rachel explains how to enjoy Credit Card Points without triggering surprise tax issues. You will learn when redeemed rewards are taxable, why statement credits can raise your net income, and how to keep personal and business spending clean in your books. We cover S corp vs LLC considerations, meal and travel documentation, mileage logs, referral 1099s, bank bonus interest, and annual fee treatment. With simple systems like QuickBooks or Excel, you can track costs, reconcile accounts, and maximize Credit Card Points the right way. If you love Points & Miles but want to stay compliant, this is your playbook. Subscribe to never miss an episode. Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Rachel’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Bonus: How to Travel to Thailand on Credit Card Points and Save Over $16,000 | 16 Sep 2025 | 00:30:14 | |
(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 113 of World Travel Made Easy With Itinerary Boss, we unpack our honeymoon to Thailand using Points & Miles. You’ll learn how we timed award availability for Qatar Qsuites via British Airways Executive Club, why positioning flights matter, and how to mix boutique hotels with big chains to keep earning. From Bangkok to Chiang Mai to Phuket, we keep this actionable and beginner friendly so you can turn Points & Miles into real trips. We cover Grab rides, Bangkok highlights, an ethical Elephant Nature Park visit, a Chiang Mai cooking class, and when to consider Krabi or Phi Phi day trips instead of overnight stays. You’ll hear lessons learned, including a heat exhaustion scare, how flexible bookings saved our plans, and what to do when ferries or flights slip. If you’re new to Points & Miles, we also touch on transfer partners and simple travel credit card points tactics without getting lost in jargon. Subscribe for more episodes that help you plan smarter and travel better. Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Itinerary Boss Socials: | |||
| How Points Path Helps You Decide Whether to Use Points or Cash on Flights with Julian Kheel | 10 Sep 2025 | 00:41:31 | |
(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 112 of World Travel Made Easy With Itinerary Boss, we sit down with Julian Keel, founder and CEO of Points Path, to make points and miles simple. If flights feel pricey and planning feels chaotic, this conversation shows how to turn everyday spend into real travel wins. Discover how Points Path layers onto Google Flights to reveal award availability, partner options, and clear value arrows that compare cash vs miles. We cover the free version for the big five programs and the Pro features like price alerts, points calendars, and custom valuations. You will learn practical points and miles strategies, when to avoid basic economy, and how transfer partners like Avios and Aeroplan unlock hidden value. If you hold flexible rewards from Amex, Chase, Capital One, or Citi, you will see where they deliver the best results. Points and Miles are the focus throughout, with clear steps to save both time and money. Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Julian’s Social Media:Instagram Itinerary Boss Socials: Pinterest 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. | |||
| Roves Miles: How to Earn, Redeem, and Travel More Points without a New Credit Card | 09 Sep 2025 | 00:30:51 | |
(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 111 of World Travel Made Easy With Itinerary Boss we sit down with Carissa Rawson to unpack Rove, a new way to earn transferable rewards without opening another card. If you want simple ways to grow points and miles, stack rewards on hotel bookings, and triple dip on flights, this conversation shows you where the value really is. We start with the basics, then move into real examples like gift cards for everyday spend, high hotel multipliers, and portal redemptions that price at 1.49 cents per point. You will also hear how Rove searches both cash fares and live award availability in one view, why some non chain hotels can beat classic transfer plays, and how transfer partners like Flying Blue, Finnair Avios, Cathay Asia Miles, and Air India Flying Returns open new routes. Whether you are new to points and miles or want faster wins, you will leave with practical steps and a clearer plan. Subscribe to stay updated on our two part series. Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Itinerary Boss Socials: Pinterest 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. | |||
| How Entrepreneurs Earn First-Class Flights: DeAndre Coke on Business Credit Cards, Status Shortcuts, and Redemptions | 03 Sep 2025 | 01:03:09 | |
(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 110 of World Travel Made Easy with Itinerary Boss, I’m joined by DeAndre Coke—financial advisor, CEO of Truist City Wealth Management, and host of the Revolutionizing Your Journey podcast—who shares how he turned $4,100 and 551,000 points into a $56,000 Maldives getaway. From Qatar Q-Suites to Emirates First Class, DeAndre reveals the exact strategies he uses to combine elite status, smart card spend, and flexible travel dates for once-in-a-lifetime experiences. We also break down how business owners can transform everyday expenses into massive point hauls, the Platinum Pro to Globalist hotel status shortcut, and how to earn American Airlines miles passively with Bask Bank. Whether you’re a first-time points user or chasing aspirational redemptions, DeAndre’s approach blends financial expertise with adventurous travel planning you can start applying right now. Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! DeAndre's Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Tools to Use When Vendor Doesn’t Take Credit Card and Why You Shouldn’t Worry About the 3% Fee | 02 Sep 2025 | 00:15:52 | |
(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 109 of World Travel Made Easy With Itinerary Boss, Ross breaks down one of the biggest misconceptions business owners have about points and miles: credit card fees. Too many entrepreneurs miss out on millions of points because they avoid the 3 percent processing fee vendors often charge. In this episode, Ross shows why those fees are tiny compared to the massive value of transferable travel rewards. Discover how tools like Melio and Plastiq help you pay contractors, real estate vendors, or even home renovators with a credit card—and why a $5,000 payment could mean a 100,000-point welcome bonus. You’ll learn how to run the numbers, compare cashback versus travel rewards, and see real examples of clients who’ve unlocked $46,000+ in free travel just by shifting how they pay expenses. Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Itinerary Boss Socials: Pinterest 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. | |||
| Credit Card Rewards for Homeowners: Travel Points & Miles on Your Mortgage, Daycare, Costco, and Home Projects with Mesa CEO Kelley Halpin | 27 Aug 2025 | 00:31:46 | |
(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 108 of World Travel Made Easy With Itinerary Boss, Ross sits down with Kelley Halpin, CEO and founder of Mesa, to explore an exciting breakthrough in credit card rewards earning points on your mortgage. For years, travelers and homeowners alike have been searching for ways to maximize their biggest expenses, and Mesa delivers by turning monthly mortgage payments, daycare, Costco runs, and even pet food into valuable points. Join us as Kelley shares the vision behind Mesa, the unique benefits of the Homeowner Card, and how families can finally align their spending with the rewards they deserve. Listeners will discover how Mesa’s Visa partnership unlocks multipliers for groceries, gas, and home projects, plus how refinancing through Mesa can deliver hundreds of thousands of points in a single transaction. From transfer partners like Air Canada and Finnair to redeeming points directly toward mortgage payments, Mesa is reshaping what it means to earn and redeem travel rewards. Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Kelley’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Credit Card Points & Travel Tips: Unlocking Transfer Partners, Airline Alliances & High-Value Redemptions for Smarter Travel | 26 Aug 2025 | 00:27:09 | |
(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 107 of World Travel Made Easy With Itinerary Boss, we dive deep into the best ways to redeem your credit card points so you can stop wasting rewards and start traveling smarter. Too many professionals, entrepreneurs, and business owners earn points but use them for statement credits or gift cards—leaving massive value on the table. Join us as we break down the world of transfer partners, airline alliances, and real-life redemption strategies that can turn 15,000 points into $400+ flights or 100,000 points into business class trips across the globe. You’ll discover how to use programs like British Airways Avios, Air Canada Aeroplan, and Virgin Atlantic for sweet spots, why Hyatt remains one of the best hotel transfer options, and how transfer bonuses can multiply your rewards by 30% or more. Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Itinerary Boss Socials: Pinterest 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. | |||
| Travel & Shopping Portals: Step-by-Step Guide to Earning More Points and Miles with Rakuten and SaveWise Tools | 21 Aug 2025 | 00:19:16 | |
(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 106 of World Travel Made Easy with Itinerary Boss, we dive into how everyday online shopping can turn into free flights and hotel stays using Rakuten and SaveWise. These two free Chrome extensions make it effortless to earn cashback, credit card points, and airline miles while shopping at your favorite stores. Imagine booking a $500 Viator tour and stacking over 6,000 points toward your next trip without spending anything extra. Rakuten allows you to choose between cashback or American Express Membership Rewards points, letting you maximize every purchase. SaveWise takes things further by comparing portals and showing you which option Amex, Chase, Citi, or even airline-specific programs like American AAdvantage—gives you the most value. Together, these tools create a powerful system that helps you double dip on rewards while planning travel or just doing everyday shopping. Website: Credit Card Resources: Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points
Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles CardPointers: Earn more from your credit cards daily
Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Function Health: Optimize your health, explore the world! Itinerary Boss Socials: Pinterest 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. | |||
| This App is the Future of Networking: Helping You with Travel, Business Growth and Real Connections with Eric Creekmore | 20 Aug 2025 | 00:31:44 | |
(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 105 of “World Travel Made Easy with Itinerary Boss,” relationship capital, Thr Technologies, and AI relationship intelligence take center stage in this conversation with Eric Creekmore. We dive into how an AI-powered personal strategist can turn missed connections into measurable opportunities, solve the timing-and-trust problem in today’s networking, and transform how business travelers connect. Eric reveals how verifiable introductions, local-only data, and a future “relationship capital” score could make conference follow-ups faster, warmer, and more effective. If you want fewer cold pitches and more trusted referrals, this episode is your blueprint for smarter, more strategic networking. Website: itineraryboss.com TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Make.com: Build Smarter Automated Workflows with no code Function Health: Optimize your health, explore the world! Carry: The modern Solo 401(k) for business owners Eric Creekmore’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| The Ultimate Guide to Germany and Oktoberfest on Points | 19 Aug 2025 | 00:12:17 | |
(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 104 of World Travel Made Easy with Itinerary Boss, Ross breaks down exactly how to use credit card points and miles to book flights to Munich and Berlin, plus how to redeem hotel points for free nights during your stay. From Lufthansa sweet spots through Aeroplan to Turkish Miles & Smiles redemptions on United, you’ll hear step-by-step strategies to save thousands on your next trip. You’ll also get a ready-made 3-day itinerary for Munich and Berlin. From Oktoberfest beer tents and the Hofbräuhaus to the BMW Museum, English Garden, Brandenburg Gate, and the Berlin Wall, this trip combines must-see highlights with local experiences. Learn how to maximize Hyatt, Hilton, and Marriott hotel stays, plus discover travel tools like Seats.Aero, Gondola AI, and Points Path to compare cash vs. points. Website: itineraryboss.com TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Make.com: Build Smarter Automated Workflows with no code Function Health: Optimize your health, explore the world! Carry: The modern Solo 401(k) for business owners Itinerary Boss Socials: Pinterest 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. | |||
| How Business Owners Should Hire an Assistant and Best Practices for using Credit Cards for Daily Expenses | 13 Aug 2025 | 00:59:16 | |
(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 103 of World Travel Made Easy with Itinerary Boss, Ross sits down with Jaime Jay, founder of Bottleneck Distant Assistance, to explore the power of hiring virtual assistants, documenting systems, and building a business that runs smoothly—even while you travel. Jaime shares his Delegation Intelligence Framework and how it’s helped countless entrepreneurs regain their time and focus. From leveraging high-limit business credit cards to pay $75K+ in monthly expenses, to exploring tools like Zil Money, Melio, and custom AI solutions, this episode dives into the real strategies modern entrepreneurs need. Whether you're just thinking about your first hire or ready to systematize your team, you’ll walk away with actionable steps to grow your business and earn rewards at the same time. Jaime's Social Media Link: Website: itineraryboss.com TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Make.com: Build Smarter Automated Workflows with no code Function Health: Optimize your health, explore the world! Carry: The modern Solo 401(k) for business owners Itinerary Boss Socials: Pinterest 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. | |||
| Unlock Massive Value with Credit Card Transfer Bonuses | 12 Aug 2025 | 00:10:38 | |
(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 102 of World Travel Made Easy with Itinerary Boss, Learn how to maximize every point you’ve earned in this episode of World Travel Made Easy with Itinerary Boss. Ross breaks down the exact strategies he uses to transfer points from credit cards like Chase and Capital One to travel partners like British Airways, Qatar, and Hyatt. He explains the value behind each airline alliance, the mechanics of transfer timing, and why being an Executive Club member is key for some redemptions. You’ll also get actionable next steps: from checking availability before transfers to creating loyalty accounts with airline and hotel partners for faster redemptions. Whether you’re a business owner with hundreds of thousands of points or a beginner planning your first trip, this episode gives you the tools to book smarter and travel further. Don’t forget to subscribe and share—it’s the best way to level up your travel game. Website: itineraryboss.com TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Make.com: Build Smarter Automated Workflows with no code Function Health: Optimize your health, explore the world! Carry: The modern Solo 401(k) for business owners Itinerary Boss Socials: Pinterest 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. | |||
| The Ultimate Guide to Prague & Budapest | 07 Aug 2025 | 00:15:58 | |
(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 101 of “World Travel Made Easy with Itinerary Boss,” Ross shares insider strategies for visiting Prague and Budapest using credit card points and AI-powered tools. Learn how to leverage Aeroplan, TAP Portugal, and ANA stopovers to add bonus destinations, find top hotels using Gondola AI, and map out unforgettable European itineraries with ChatGPT’s Plus/Terminal mode. Ross also shares must-do activities like the Hungarian Parliament tour and Danube River cruises, along with specific lodging tips for both cities. Whether you’re planning a trip this fall or already dreaming about Europe 2025, this episode is packed with tools, apps, and Award Travel insights that will help you save money, travel smarter, and enjoy the journey. Website: itineraryboss.com TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Make.com: Build Smarter Automated Workflows with no code Function Health: Optimize your health, explore the world! Carry: The modern Solo 401(k) for business owners Itinerary Boss Socials: Pinterest 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. | |||
| How Busy Sales Moms and Women Business Owners Can Travel Better Using Credit Card Points with Leslie Douglas | 06 Aug 2025 | 00:50:21 | |
(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 100 of World Travel Made Easy with Itinerary Boss, Ross and Leslie for a deep-dive into how business owners, parents, and sales leaders can unlock smarter travel using points, systems, and savings strategies. From automating finances to maximizing loyalty programs, they unpack practical tactics that support both career growth and family adventures. Leslie shares her parenting travel toolkit, including must-pack items and routines that help kids feel grounded even on the go. Ross opens up about recent wins with credit card automation tools and previews a special guest appearance by the CEO of CardPointers. Whether you’re a busy entrepreneur or a parent trying to build memories on a budget, this milestone episode offers inspiration and actionable tips for the road ahead. Website: itineraryboss.com TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Make.com: Build Smarter Automated Workflows with no code Function Health: Optimize your health, explore the world! Carry: The modern Solo 401(k) for business owners Leslie’s Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Transfer Partners 101: How to Maximize Credit Card Points for Flights, Hotels, and Free Travel | 05 Aug 2025 | 00:12:39 | |
(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 99 of World Travel Made Easy with Itinerary Boss, Learn how to maximize every point you’ve earned in this episode of World Travel Made Easy with Itinerary Boss. Ross breaks down the exact strategies he uses to transfer points from credit cards like Chase and Capital One to travel partners like British Airways, Qatar, and Hyatt. He explains the value behind each airline alliance, the mechanics of transfer timing, and why being an Executive Club member is key for some redemptions. You’ll also get actionable next steps: from checking availability before transfers to creating loyalty accounts with airline and hotel partners for faster redemptions. Whether you’re a business owner with hundreds of thousands of points or a beginner planning your first trip, this episode gives you the tools to book smarter and travel further. Don’t forget to subscribe and share—it’s the best way to level up your travel game. Website: itineraryboss.com TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Make.com: Build Smarter Automated Workflows with no code Rakuten : Earn cash back on every purchase! Function Health: Optimize your health, explore the world! Carry: The modern Solo 401(k) for business owners Itinerary Boss Socials: Pinterest 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. | |||
| How Credit Cards can Pay for Family Vacations + How to Teach Your Kids Points and Miles with the Points Mom | 30 Jul 2025 | 00:52:32 | |
(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 98 of World Travel Made Easy with Itinerary Boss, Ross chats with Cindy, aka “The Points Mom,” about her journey from crunching numbers to maximizing miles. Learn how she saved over $5,000 on an Aspen ski trip using hotel points, helped her kids build credit starting at age 18, and why she swears by flexible rewards cards over co-branded options. This episode breaks down real-world strategies for managing multiple credit cards, avoiding interest traps, timing applications around high-spend periods, and making the most of business expenses. Whether you're planning a safari with points or just trying to raise credit-smart kids, Cindy’s advice offers both big wins and peace of mind for families navigating the world of travel rewards. Website: itineraryboss.com TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Make.com: Build Smarter Automated Workflows with no code Function Health: Optimize your health, explore the world! Carry: The modern Solo 401(k) for business owners Cindy's Social Media: Itinerary Boss Socials: Pinterest 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. | |||
| Ultimate Credit Card Strategy for Couples: Learn the Step by Step Two Player Mode Strategy | 29 Jul 2025 | 00:17:22 | |
(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 97, Discover the best travel credit card strategies for couples in this episode of World Travel Made Easy with Itinerary Boss. Ross breaks down “2 Player Mode,” a game-changing approach that helped him and his wife open 9 cards, save $25,000, and rack up 660,000 points. Learn how to check your 5/24 status, evaluate your current cards, and pick the right anchor travel card to start your journey. Ross also shares tactical tips for aligning card applications with upcoming trips, using no-fee and 0% APR cards strategically, and making the most of quarterly promos. Whether you’re just getting started or ready to level up, this episode gives you the map to travel smarter as a team. Website: itineraryboss.com TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Kit: Grow and monetize your email list ClickUp: Stay organized and master projects Make.com: Build Smarter Automated Workflows with no code Function Health: Optimize your health, explore the world! Carry: The modern Solo 401(k) for business owners Itinerary Boss Socials: Pinterest 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. | |||