(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.
(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.
(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.
(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.
(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 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.
(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, 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.
(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.
(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:
(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.
(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.
(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.
(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.
(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.
(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.
(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.
(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!
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
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.
(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!
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.
(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!
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.
(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!
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.
(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!
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.
