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(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
Best Credit Cards for Travel
Bonus Offer Notifications
Transfer Bonus Notifications
Points and Miles Cheat Sheet
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:
Instagram
Itinerary Boss Socials:
Instagram
Pinterest
Facebook
YouTube
Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.
Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.
By Ross Alcorn5
1717 ratings
(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
Best Credit Cards for Travel
Bonus Offer Notifications
Transfer Bonus Notifications
Points and Miles Cheat Sheet
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:
Instagram
Itinerary Boss Socials:
Instagram
Pinterest
Facebook
YouTube
Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.
Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

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