The $580,000 Mistake That's Quietly Draining Business Owners' Travel Budgets

How to Plan a Stress-Free Trip: Flight Alerts, Travel Apps, and the Documents You Can't Afford to Forget

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as⁠ YourBestCreditCards.com⁠ [https://yourbestcreditcards.com/?ccid=2015]. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired. In episode 156 of Points, Cards and Travel, Ross walks through the ultimate pre-trip planning and vacation document checklist, the exact system he's refined over 10+ years of travel mistakes so you don't have to repeat them. Before diving into documents, Ross covers the planning fundamentals: figuring out your travel style, setting up flight alerts through Google Flights, Skyscanner, or the Capital One travel portal, and choosing the right apps to manage your itinerary (Google Docs, Google Maps, TripIt, Viator, and more).   From there, he breaks down the full document checklist for any trip, domestic or international, including visas and vaccinations, backup flight and accommodation confirmations, travel insurance (and which credit card benefits actually cover it), car rental and tour ticket downloads, emergency contacts, and passport copies. Ross also shares his cash and currency strategy for avoiding hidden transaction fees abroad, plus why splitting your cards, cash, and IDs across bags can save a trip when something goes wrong. If you want all of this compiled for you, Ross's free Stress-Free Travel Starter Kit has the entire checklist ready to go. Next week: the vacation packing checklist. Credit Card Resources: ⁠5 Step Roadmap⁠ to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There [https://itineraryboss.kit.com/the-5-step-roadmap-to-your-next-free-5-star-luxury-vacation-the-1-card-that-gets-you-there?utm_source=ig&utm_medium=social&utm_content=link_in_bio&fbclid=PAZXh0bgNhZW0CMTEAc3J0YwZhcHBfaWQMMjU2MjgxMDQwNTU4AAGnsnF8N-YlYgYUH_EhRJC7AwZ0aIH70M1qm5JXFVv-gCqdXroCyTW31OtKPMs_aem_bpWd4IdukfBTmp39vl9hmg] Best Credit Cards for Travel [https://yourbestcreditcards.com/?ccid=2015] Melio [https://affiliates.meliopayments.com/f5l0dow7na3w]: Pay vendors who don't take card with credit card to earn more points Itinerary Boss Socials: ⁠LinkedIn⁠ [https://www.linkedin.com/in/rossalcornru/] ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ [https://www.instagram.com/itineraryboss/] ⁠⁠⁠⁠ [https://www.instagram.com/itineraryboss/]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.pinterest.com/itineraryboss/]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.tiktok.com/@itineraryboss?_t=8jUaFIFrI0R&_r=1] ⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.facebook.com/share/g/kg9fQpBYdDq3nAW8/?mibextid=K35XfP] ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.youtube.com/@ItineraryBoss]  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.youtube.com/@ItineraryBoss]Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.   Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

How Business Owners Turn Everyday Expenses Into Free Family Vacations

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as⁠ YourBestCreditCards.com⁠ [https://yourbestcreditcards.com/?ccid=2015]. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired. In episode 154 of Points, Cards and Travel, Ross sits down with Leslie Douglas, VP of Sales at Sell Better, sales trainer, podcast host, and self-described "Delta girly and Marriott girly." Leslie shares how she balances life on the road (30-40% travel) as a mom while building a points strategy that's covered nearly free trips, including an $80 all-in trip to New York with her daughter. The conversation dives into business expense strategies, including Leslie's story of putting a $10,000 car down payment on her American Express card for instant elite status, why every reimbursable expense should go on your personal card, and how recurring business costs can be converted into travel rewards.  They also cover tools like Card Pointers Pro and Rakuten for stacking offers, the importance of picking an airline/hotel "home base," and simple money habits like automated high-yield savings accounts for funding future trips. Whether you're a sales rep, business owner, or frequent traveler with kids, this episode is packed with practical, real-world strategies for traveling more without spending more.  Credit Card Resources: ⁠5 Step Roadmap⁠ to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There [https://itineraryboss.kit.com/the-5-step-roadmap-to-your-next-free-5-star-luxury-vacation-the-1-card-that-gets-you-there?utm_source=ig&utm_medium=social&utm_content=link_in_bio&fbclid=PAZXh0bgNhZW0CMTEAc3J0YwZhcHBfaWQMMjU2MjgxMDQwNTU4AAGnsnF8N-YlYgYUH_EhRJC7AwZ0aIH70M1qm5JXFVv-gCqdXroCyTW31OtKPMs_aem_bpWd4IdukfBTmp39vl9hmg] Best Credit Cards for Travel [https://yourbestcreditcards.com/?ccid=2015] Melio [https://affiliates.meliopayments.com/f5l0dow7na3w]: Pay vendors who don't take card with credit card to earn more points Leslie’s Social Media: ⁠LinkedIn⁠ [https://www.linkedin.com/in/lesliebdouglas/] ⁠Instagram [https://www.instagram.com/itslesliedouglas/] Itinerary Boss Socials: ⁠LinkedIn⁠ [https://www.linkedin.com/in/rossalcornru/] ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ [https://www.instagram.com/itineraryboss/] ⁠⁠⁠⁠ [https://www.instagram.com/itineraryboss/]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.pinterest.com/itineraryboss/]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.tiktok.com/@itineraryboss?_t=8jUaFIFrI0R&_r=1] ⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.facebook.com/share/g/kg9fQpBYdDq3nAW8/?mibextid=K35XfP] ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.youtube.com/@ItineraryBoss]  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.youtube.com/@ItineraryBoss]Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.   Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

The $580,000 Mistake That's Quietly Draining Business Owners' Travel Budgets

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as⁠ YourBestCreditCards.com⁠ [https://yourbestcreditcards.com/?ccid=2015]. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired. In episode 154 of Points, Cards and Travel, most business owners avoid credit cards for vendor payments because of the 3% processing fee, but that mindset could be costing them millions of points. In this episode, Ross breaks down how tools like Plastiq and Melio let you pay contractors, vendors, and service providers who only accept cash or check using a credit card, unlocking massive points-earning potential.  Ross walks through real numbers: a $580,000 annual spend turning into $46,000+ of travel value, and how scaling to 3-5x multipliers can push that even higher. Whether you're a real estate investor, house flipper, or business owner working with old-school vendors, this episode shows you how a simple two-card stack and the right software can transform routine expenses into life-changing travel rewards.  Credit Card Resources: ⁠5 Step Roadmap⁠ to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There [https://itineraryboss.kit.com/the-5-step-roadmap-to-your-next-free-5-star-luxury-vacation-the-1-card-that-gets-you-there?utm_source=ig&utm_medium=social&utm_content=link_in_bio&fbclid=PAZXh0bgNhZW0CMTEAc3J0YwZhcHBfaWQMMjU2MjgxMDQwNTU4AAGnsnF8N-YlYgYUH_EhRJC7AwZ0aIH70M1qm5JXFVv-gCqdXroCyTW31OtKPMs_aem_bpWd4IdukfBTmp39vl9hmg] Best Credit Cards for Travel [https://yourbestcreditcards.com/?ccid=2015] Melio [https://affiliates.meliopayments.com/f5l0dow7na3w]: Pay vendors who don't take card with credit card to earn more points Itinerary Boss Socials: ⁠LinkedIn⁠ [https://www.linkedin.com/in/rossalcornru/] ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ [https://www.instagram.com/itineraryboss/] ⁠⁠⁠⁠ [https://www.instagram.com/itineraryboss/]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.pinterest.com/itineraryboss/]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.tiktok.com/@itineraryboss?_t=8jUaFIFrI0R&_r=1] ⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.facebook.com/share/g/kg9fQpBYdDq3nAW8/?mibextid=K35XfP] ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.youtube.com/@ItineraryBoss]  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.youtube.com/@ItineraryBoss]Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.   Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

Why Your Business Should Accept Every Form of Payment and How to Use That Spend to Fund Your Next Trip With David C. Barnett

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as⁠ YourBestCreditCards.com⁠ [https://yourbestcreditcards.com/?ccid=2015]. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired. In episode 153 of Points, Cards and Travel, Ross sits down with David C. Barnett, host of Small Business and Deal Making, to talk about one of the most overlooked opportunities for small business owners, using everyday business spending to earn credit card points, reduce tax burden, and fund luxury travel. David brings a unique perspective as a former American Express rep who spent years helping business owners and CFOs build corporate card strategies. Together, he and Ross break down the real math behind the 3% vendor fee, how to run a vendor analysis to find where cards are already accepted, why float can function like interest-free operating capital, and how accepting every form of payment actually becomes a competitive advantage. Credit Card Resources: ⁠5 Step Roadmap⁠ to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There [https://itineraryboss.kit.com/the-5-step-roadmap-to-your-next-free-5-star-luxury-vacation-the-1-card-that-gets-you-there?utm_source=ig&utm_medium=social&utm_content=link_in_bio&fbclid=PAZXh0bgNhZW0CMTEAc3J0YwZhcHBfaWQMMjU2MjgxMDQwNTU4AAGnsnF8N-YlYgYUH_EhRJC7AwZ0aIH70M1qm5JXFVv-gCqdXroCyTW31OtKPMs_aem_bpWd4IdukfBTmp39vl9hmg] Best Credit Cards for Travel [https://yourbestcreditcards.com/?ccid=2015] Melio [https://affiliates.meliopayments.com/f5l0dow7na3w]: Pay vendors who don't take card with credit card to earn more points David’s Social Media: Instagram [https://www.instagram.com/dbarnettmoncton/] Website [https://www.investlocalbook.com/] YouTube [https://www.youtube.com/@DavidCBarnett] Itinerary Boss Socials: ⁠LinkedIn⁠ [https://www.linkedin.com/in/rossalcornru/] ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ [https://www.instagram.com/itineraryboss/] ⁠⁠⁠⁠ [https://www.instagram.com/itineraryboss/]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.pinterest.com/itineraryboss/]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.tiktok.com/@itineraryboss?_t=8jUaFIFrI0R&_r=1] ⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.facebook.com/share/g/kg9fQpBYdDq3nAW8/?mibextid=K35XfP] ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.youtube.com/@ItineraryBoss]  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.youtube.com/@ItineraryBoss]Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.   Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

How Homeowners and Landlords Can Earn Massive Points on Real Estate, Renovations, Contractors, and Mortgage Payments With Ross Alcorn

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as⁠ YourBestCreditCards.com⁠ [https://yourbestcreditcards.com/?ccid=2015]. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired. In episode 152 of Points, Cards and Travel, Ross joins Mary Ellen and Jo from Wonderland on Points to break down one of the most overlooked areas in the points and miles world — real estate and home spending. If you own a home, manage rental properties, or are about to furnish a new space, this episode shows you exactly how to turn those expenses into serious travel rewards. Ross walks through his personal property portfolio, the strategies he uses to separate business and personal spend, and how tools like Plastiq make it possible to earn points even when contractors only take cash. They also dig into the Mesa card and why homeowners finally have a way to earn points on mortgage payments, Costco purchases, and home renovation projects. Credit Card Resources: ⁠5 Step Roadmap⁠ to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There [https://itineraryboss.kit.com/the-5-step-roadmap-to-your-next-free-5-star-luxury-vacation-the-1-card-that-gets-you-there?utm_source=ig&utm_medium=social&utm_content=link_in_bio&fbclid=PAZXh0bgNhZW0CMTEAc3J0YwZhcHBfaWQMMjU2MjgxMDQwNTU4AAGnsnF8N-YlYgYUH_EhRJC7AwZ0aIH70M1qm5JXFVv-gCqdXroCyTW31OtKPMs_aem_bpWd4IdukfBTmp39vl9hmg] Best Credit Cards for Travel [https://yourbestcreditcards.com/?ccid=2015] Melio [https://affiliates.meliopayments.com/f5l0dow7na3w]: Pay vendors who don't take card with credit card to earn more points Wonderland On Points Social Media: Instagram [https://www.instagram.com/wonderlandonpointspodcast/] Apple Podcast [https://podcasts.apple.com/us/podcast/wonderland-on-points-credit-card-rewards-budget-travel/id1718475603] Spotify Podcast [https://open.spotify.com/show/0MWRbEbtZcqKPXaWdDuTXM?si=814ddecb7bc24ae1] Itinerary Boss Socials: ⁠LinkedIn⁠ [https://www.linkedin.com/in/rossalcornru/] ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ [https://www.instagram.com/itineraryboss/] ⁠⁠⁠⁠ [https://www.instagram.com/itineraryboss/]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.pinterest.com/itineraryboss/]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.tiktok.com/@itineraryboss?_t=8jUaFIFrI0R&_r=1] ⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.facebook.com/share/g/kg9fQpBYdDq3nAW8/?mibextid=K35XfP] ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.youtube.com/@ItineraryBoss]  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ [https://www.youtube.com/@ItineraryBoss]Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.   Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.