(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 150 of Points, Cards and Travel, Ross Alcorn joins DeAndre Coke to break down how he turned everyday spending into nearly $20,000 in luxury travel using a simple, strategic approach to points and miles. If you’ve ever wondered how to maximize points and miles without overcomplicating your setup, this episode gives you a clear roadmap built on real results.

Discover how Ross leveraged business expenses, group travel planning, and credit card strategy to fund business class flights, high-end hotels, and an unforgettable honeymoon experience. They dive into practical ways to earn points faster, avoid common mistakes, and use tools like loyalty programs, transferable points, and welcome bonuses to unlock outsized value. You’ll also learn how to approach real estate spending, vendor payments, and large life events like weddings as opportunities to accelerate rewards.

Credit Card Resources:

⁠5 Step Roadmap⁠ to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There

Best Credit Cards for Travel

Melio: Pay vendors who don't take card with credit card to earn more points

DeAndre’s Social Media:

Instagram

Itinerary Boss Socials:

⁠LinkedIn⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠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.