Tag: Credit Card Strategy

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The Psychology of Points: Mastering Behavior, Not Bonuses (Ep. 77)

The Psychology of Points: Mastering Behavior, Not Bonuses (Ep. 77)

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This episode isn’t about earning your next big bonus or finding the hottest travel deal—it’s about the mindset that makes all of it sustainable. 

DeAndre Coke shares a powerful solo session unpacking how mastering points and miles is less about tactics and more about behavior. Drawing insights from the book “The Psychology of Money” and over a decade of advising experience, he explains why understanding your habits, defining your version of “enough,” embracing optionality, and building identity-driven financial discipline can unlock not just better travel, but a better life. 

If you’re ready to stop chasing and start strategizing, this one’s for you.

 

Key Highlights:

  • Behavior > Bonuses: Winning with points is about patience and discipline, not just card hacks.
  • Define “Enough”: Set intentional goals to avoid endlessly chasing bigger redemptions.
  • Optionality = Power: Having points gives you choices—and that’s where absolute travel freedom begins.
  • Hedonic Adaptation: The more you redeem, the more you adapt—learn to appreciate and recalibrate.
  • Delayed Gratification: Waiting for the proper redemption often leads to the most significant wins.
  • Diversification Matters: Don’t hoard points in one program; spread risk and gain flexibility.
  • Self-Sabotage is Real: Overspending for bonuses or never redeeming points are behavioral pitfalls.
  • Identity Drives Action: Seeing yourself as a savvy strategist helps you naturally make better decisions.
  • Quiet Accumulation Pays: Consistent, smart habits lead to long-term travel wealth.
  • Points as Practice: This is more than travel—it’s training for financial self-mastery.

 

Resources:

 

Interested in Financial Planning?

 

Some of Our Favorite Tools For Elevating Your Points & Miles Game:

Note: Contains affiliate/sponsored links

 

Connect with DeAndre Coke: 

 

 

 

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Are Credit Card Points Taxable? A CPA Explains What the IRS Actually Cares About with Rachel Earl (Ep. 75)

Are Credit Card Points Taxable? A CPA Explains What the IRS Actually Cares About with Rachel Earl (Ep. 75)

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Are your points and miles taxable?

 In this episode, host DeAndre Coke is joined by CPA Rachel Earl to demystify the often-confusing world where travel rewards and taxes meet. They unpack how the IRS views points earned from credit card sign-up bonuses, referral links, and cashback programs, and clarify when travel rewards might be considered income.

The conversation also dives into smart tax planning strategies that can earn you valuable points—like paying estimated taxes by card—and covers key insights around bank bonuses, QuickBooks tracking, and business credit card usage. Rachel shares her professional insights as well as personal travel tips, offering a rare intersection of finance, strategy, and wanderlust. This episode is a must-listen for anyone looking to navigate the financial side of travel rewards with more clarity and confidence.

 

Key Highlights:

  • Points vs. taxes: Points and miles from sign-up bonuses are not taxable, but referral bonuses may be.
  • IRS guidance: Current IRS rulings on this topic haven’t been updated since 2002.
  • Cashback simplicity: Cash back is generally not considered taxable income.
  • Credit card usage: Personal cards can be used for business expenses with proper documentation.
  • IRS priorities: The IRS does not track individual cardholders or card usage patterns.
  • Bank bonuses: These are reported on 1099-INT forms and are treated as interest income.
  • W2 caution: W2 employees should be careful when opening a business entity for points purposes.
  • Estimated tax payments: Can be used to earn points, but risks and limits apply—especially in states like California.
  • Record-keeping: QuickBooks or other tracking tools help streamline expense categorization.
  • Wanderlog for travel: A useful tool for organizing travel plans and expenses.

 

This episode is sponsored by Saily. Use Code BOLDLYGO for a 15% discount

 

Resources:

 

Interested in Financial Planning?

 

Some of Our Favorite Tools For Elevating Your Points & Miles Game:

Note: Contains affiliate/sponsored links

 

CPA’s Footnotes:

 

Connect with DeAndre Coke: 

 

Connect with Rachel Earl:

 

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Quick Hits: Hyatt Adds The Standard Hotels, Emirates First Class Lockdown, Rakuten Promo Alert & More!

Quick Hits: Hyatt Adds The Standard Hotels, Emirates First Class Lockdown, Rakuten Promo Alert & More!

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Planning your summer 2025 travel? Now might be the perfect time to book. 

In this Quick Hits episode, DeAndre Coke shares key updates from his recent trip to Roatan and fresh news in the points and miles world. He covers limited-time transfer bonuses, how to spot travel savings on previously booked trips, and why Rakuten’s 7,500 Amex point promo is worth jumping on. You’ll also hear why Newark Airport might be best avoided for now, how Hyatt integrates The Standard hotels, and what Hyatt’s new gifting rules mean for loyal travelers. 

Finally, DeAndre breaks down Emirates’ move to restrict first-class redemptions and how to still unlock the experience through strategic credit card plays.

 

Key takeaways: 

  • Roatan reflections: A surprisingly incredible stay at the Grand Kimpton Roatan, made better with points and Amex FHR perks.
  • Summer 2025 alert: Now is the sweet spot for booking cheap domestic flights before prices spike.
  • Travel disruptions: Newark Airport is seeing significant delays and cancellations—consider alternative routes.
  • Booking tip: Already booked a summer trip? Check current pricing—DeAndre saved $300 and 70k Hyatt points on a rebook.
  • Rakuten promo: New users can get 7,500 Amex points with just $25 in spending through Rakuten.
  • Hyatt & The Standard: The Standard hotels officially join World of Hyatt with elite perks intact.
  • Award gifting limits: Hyatt will limit members to 10 award gifts received per year starting June 7.
  • Emirates first-class restrictions: As of May 12, only Skywards elite members can redeem for first class.
  • Credit card workaround: Get Emirates Silver or Gold elite status through co-branded Skywards cards to retain access.

 

Resources:

 

Interested in Financial Planning?

 

Some of Our Favorite Tools For Elevating Your Points & Miles Game:

Note: Contains affiliate/sponsored links

Connect with DeAndre Coke: 

 

 

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Planning the Ultimate F1 Grand Prix Experience on Points with Jenna of @travelersinlaw (Ep. 71)

Planning the Ultimate F1 Grand Prix Experience on Points with Jenna of @travelersinlaw (Ep. 71)

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Ever wondered how to make luxury travel to a world-class Formula 1 race affordable? 

In this episode of Revolutionizing Your Journey, host DeAndre Coke sits down with attorney-turned-travel-hacker Jenna of @travelersinlaw to explore exactly that. Jenna shares how she went from burnout in the legal profession to building a lifestyle fueled by points and miles—one that now includes an upcoming trip to the F1 Italian Grand Prix 2025 in Monza.

They dive into how to strategically earn and redeem points, the best credit card approaches for high-value travel, and what it takes to attend global events like Formula 1 without breaking the bank. Jenna also opens up about how travel became part of her self-care routine, why it’s okay to explore without a perfect itinerary, and how busy professionals can still make unforgettable trips a reality.

This episode is packed with real-world advice, smart strategies, and inspiration for travelers looking to elevate their experiences using points and miles.

 

Key Highlights:

  • Burnout Recovery: Travel as a tool for self-care and balance.
  • Credit Strategy: Smart use of cards and bonus categories boosts rewards.
  • Monza Planning: Insight into budgeting for the 2025 Italian Grand Prix.
  • Luxury on Points: Premium hotels and flights are within reach with the right strategy.
  • F1 Travel Costs: What to expect and how to offset costs with points.
  • Flexible Itineraries: It’s okay not to plan every minute—some freedom is part of the fun.
  • Credit Scores: Managing your credit while optimizing travel benefits.
  • Busy Professionals: Why taking time off is essential—and how to make it worth it.
  • Long-Term Wins: Starting small in points and miles leads to big travel gains.

 

 

Resources:

Resources:

Interested in Financial Planning?

 

Some of Our Favorite Tools For Elevating Your Points & Miles Game:

Note: Contains affiliate/sponsored links

Connect with DeAndre Coke: 

 

Connect with Jenna:

 

 

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Quick Hits: ANA’s Devaluation, How to re-qualify for Chase’s Biggest Bonus & More!

Quick Hits: ANA’s Devaluation, How to re-qualify for Chase’s Biggest Bonus & More!

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Is ANA’s legendary around-the-world ticket going away for good?

In this Quick Hits episode, DeAndre Coke checks in from the Dominican Republic—on a site visit for his upcoming wedding—to bring you the latest news in the world of travel, points, and miles. He breaks down ANA’s significant devaluation, explains the ticking clock on booking their coveted around-the-world ticket, and clarifies who’s eligible for Chase Sapphire Preferred’s elevated 100,000-point offer.

DeAndre also shares the latest updates on Zil Money’s delayed card processing system for payroll and offers a transparent follow-up to a recent discrepancy between a podcast and Instagram about his use of points versus travel insurance for a flight delay. If you’re looking to stay sharp on offers, program updates, and real-life travel hacks, this episode is packed with practical insights—recorded right from paradise.

Tune in to stay ahead on travel strategy and loyalty program changes.

 

Key takeaways: 

  • ANA Around-the-World Ticket: Book by June 24 before ANA eliminates this aspirational redemption.
  • ANA One-Way Redemptions: ANA will finally allow one-way point bookings, offering more flexibility.
  • Chase Sapphire Preferred Bonus: A 100,000-point welcome offer is available—but only if you meet strict eligibility rules.
  • Zil Money Update: The platform is still down due to overwhelming demand; processing is expected to resume soon.
  • Travel Insurance Clarification: DeAndre confirms he used points (not cash) for a Hyatt stay during a flight delay, and breaks down how trip delay coverage varies by card.
  • Trip Delay Insurance Tip: Chase Sapphire Preferred = 12-hour delay or overnight stay; Reserve = 6-hour delay coverage.

 

Resources:

Resources:

 

Interested in Financial Planning?

 

Some of Our Favorite Tools For Elevating Your Points & Miles Game:

Note: Contains affiliate/sponsored links

Connect with DeAndre Coke: 

 

 

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Revolutionize Your Travel: Must-Have Tools to Plan, Book, and Organize Your Points & Miles Game (Ep. 69)

Revolutionize Your Travel: Must-Have Tools to Plan, Book, and Organize Your Points & Miles Game (Ep. 69)

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Have you ever wondered what tools a points and miles expert uses to book smarter, earn faster, and stay organized while traveling?

In this solo episode of Revolutionizing Your Journey, host DeAndre Coke breaks down his personal travel toolkit—from the apps that help him choose the right credit card at checkout, to the tools he swears by for booking award flights and organizing itineraries. From automating credit card offers with Card Pointers to searching for award flights with tools like PointsYeah and Seats.aero, DeAndre walks listeners through each step of his travel planning process. He also discusses the value of platforms like Zil Money for earning points on business expenses, and apps like TripIt for keeping itineraries organized. This episode offers practical insights for travelers looking to simplify and optimize their rewards-based travel. 

This post contains affiliate links for some of the products mentioned, but we personally use and pay for most of these services ourselves because we believe in their value. We want to share the best points and miles tools that have helped us maximize our travel rewards.

 

Key Highlights:

  • Card Pointers: An app that helps users choose the best credit card for each purchase and automatically loads Amex and Chase offers without logging in.
  • Zil Money: Platform that lets businesses earn points by processing payroll through credit cards—useful for hitting sign-up bonuses and earning high multipliers.
  • Travel Freely: This tool tracks credit card annual fees and sign-up bonuses and helps users comply with Chase’s 5/24 rule.
  • PointsYeah: Award flight search engine with features like Daydream Explorer and live seat maps, making it easier to spot high-value redemptions.
  • Seats.aero: A power-user tool for finding award seat availability, especially useful for last-minute and expert-level searches.
  • Points Path:  The first award flight search engine that runs directly in Google Flights, and provides both the cash price and points price of many flights.
  • FlightConnections: Visualization tool showing all direct routes between airports—great for mapping international travel and alliance-specific itineraries.
  • Boldly Go Calculators: Transfer Bonus Calculator and Point Redemption Calculator simplify reward math and show real point value.
  • Point.me: Beginner-friendly award search tool that includes step-by-step guides and Amex cardholder access for free.
  • Thrifty Traveler: Subscription service that sends alerts for award availability, mistake fares, and significant cash deals.
  • TripIt: Travel organization app that builds an itinerary from confirmation emails and syncs across devices—even offline. Helpful for keeping track of complex trips and flight changes.

 

Episodes Mentioned:

 

Resources:

 

Connect with DeAndre Coke: 

 

 

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Choice Hotels, Citi Points, and Irish Charm: A Unique Points and Miles Strategy by @thepointsflygirl (Ep. 67)

Choice Hotels, Citi Points, and Irish Charm: A Unique Points and Miles Strategy by @thepointsflygirl (Ep. 67)

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What happens when a criminal defense attorney turns her free time during the pandemic into learning about travel rewards strategies?

 In this episode of Revolutionizing Your Journey, host DeAndre Coke sits down with Deanna Keane aka @pointsflygirl, an attorney by day and a points and miles expert by passion. Deanna shares her journey into the world of points and miles, including how she leverages Citi ThankYou points, Amex Business Platinum benefits, and underappreciated programs like Choice Hotels to craft unforgettable experiences. 

From her favorite redemptions in Ireland to unique travel moments in Iceland, this conversation is packed with actionable tips for travelers looking to maximize value without sacrificing quality.

Whether you’re curious about driving in Ireland, booking with kitchenettes in Iceland, or how to score the best deals from Vegas to Dublin, Deanna breaks it down in a relatable, strategic way. Tune in and discover how smart planning, flexible redemptions, and a little creativity can unlock global adventures.

 

Key Highlights:

  • Pandemic Pivot: Deanna began exploring points and miles during COVID and found a new passion.
  • Strategic Redemptions: Citi ThankYou Points offer substantial value for everyday spending and travel.
  • Hidden Gems: Choice Hotels often provide surprisingly good redemption opportunities.
  • Ireland Tips: The Dingle Peninsula and Blarney Castle are must-visit destinations.
  • Flight Deals: KLM and British Airways offer interesting routes and redemption options.
  • Best Time to Visit Ireland: May through September offers ideal weather for exploration.
  • Drive to Discover: Renting a car in Ireland enhances the experience beyond tourist hotspots.
  • Iceland Insights: Booking hotels with kitchenettes helps save money in a pricey destination.
  • Wine Hack: You can purchase wine at the airport in Iceland—perfect for budget travelers.

 

 

Resources:

 

Connect with DeAndre Coke: 

 

Connect with Deanna Keane:

 

 

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Travel Smarter: How to Maximize Every Mile and Point with Julia Menez of @geobreezetravel (Ep. 64)

Travel Smarter: How to Maximize Every Mile and Point with Julia Menez of @geobreezetravel (Ep. 64)

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Have you ever wondered how to get the most value out of your points and miles?

In this episode of the Revolutionizing Your Journey podcast, host DeAndre Coke sits down with Julia Menez, founder of Geobreeze Travel, to break down the best strategies for maximizing travel redemptions. Julia shares her journey into the points and miles space and explains the importance of tracking travel metrics, including cents per point (CPP) and out-of-pocket cost ratios, to ensure you’re getting the best possible value.

They also discuss how to prioritize travel goals, when to opt for luxury versus budget-friendly options, and why transfer bonuses and airline partnerships can significantly enhance your travel experience. Julia highlights Hyatt’s strong redemption value, the best lounges to visit, and the benefits of tracking routes for premium travel. 

Whether you’re new to points and miles or looking to refine your strategy, this episode is packed with actionable insights to help you optimize your redemptions, minimize expenses, and elevate your travel experiences.

 

Key Highlights:

  • Tracking Metrics: Decide if tracking cents per point (CPP) or other metrics aligns with your travel goals.
  • Fun Over Stress: Points and miles should enhance travel, not add pressure.
  • Value Over Cost: Travel isn’t just about spending less; it’s about maximizing experiences.
  • Minimizing Out-of-Pocket Costs: Keeping expenses low is crucial for budget travelers.
  • Hyatt’s No-Tax Redemptions: Standard room redemptions with Hyatt don’t include additional taxes.
  • Transfer Bonuses: Using strategic transfer bonuses can significantly boost redemption value.
  • Tracking Flight Routes: Helps with planning premium cabin redemptions and maximizing luxury.
  • Best Lounges: The Pier Lounge in Hong Kong is a must-visit for Oneworld Emerald members.
  • Underrated Travel Programs: Choice Hotels and other lesser-known programs can offer great redemptions.
  • Luxury on Short Flights: High-end experiences can still be affordable on shorter routes.

 

 

Resources:

 

Connect with DeAndre Coke: 

 

Connect with Julia Menez:

 

 

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Simplifying Points & Miles: A “Lazy” Approach to Travel Rewards with Genni of @travelingfranklins (Ep. 62)

Simplifying Points & Miles: A “Lazy” Approach to Travel Rewards with Genni of @travelingfranklins (Ep. 62)

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Ever wonder how you can simplify your travel rewards strategy and maximize points with minimal effort? 

In this episode, DeAndre sits down with Genni Franklin to demystify the world of points and miles. Genni, who transitioned from the hospitality industry into travel rewards, reveals her “lazy” approach—earning points with minimal effort while still maximizing value. She explains the importance of building confidence through that all-important first redemption, clarifies the differences between flexible and non-flexible points, and shares tailored strategies for families.

Genni also highlights her top credit card recommendations and offers practical tips for streamlining the redemption process, making travel both accessible and affordable. Ultimately, she encourages listeners to focus on their unique travel goals and adopt a flexible mindset to unlock incredible opportunities.

Tune in now to learn how to simplify your rewards strategy and start maximizing your travel potential!

 

Key Highlights:

  • Simplified Approach: Genni emphasizes a “lazy” strategy that minimizes effort while maximizing points and miles.
  • Confidence Through Redemption: Building confidence by making that first successful redemption is essential.
  • Flexible Points Advantage: Understanding the difference between flexible and non-flexible points can expand your travel options.
  • Family Strategies: Tailoring travel rewards strategies for families can significantly enhance travel experiences.
  • Credit Card Recommendations: Genni shares her favorite credit cards that help maximize travel rewards.
  • Smart Budgeting: Effective travel planning and budgeting are crucial for optimizing points and miles.
  • Personal Focus: Focus on your unique travel journey rather than comparing yourself to others.
  • Embrace Flexibility: Flexibility in travel planning can unlock incredible opportunities and better deals.
  • Continuous Learning: Ongoing education about points and miles is vital for long-term success.

 

Resources:

 

Connect with DeAndre Coke: 

 

Connect with Genni Franklin:

 

 

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Quick Hits: Unlock Big Travel Perks with Chase, Southwest Companion Pass, and Marriott Bonvoy

Quick Hits: Unlock Big Travel Perks with Chase, Southwest Companion Pass, and Marriott Bonvoy

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In this Quick Hits episode, DeAndre Coke delivers a rapid breakdown of the latest offers in the points and miles world, focusing on key cards to help you boost your travel rewards. He highlights the Chase Ink Business Unlimited card’s $900 cash-back offer and shares strategies for converting cash back into travel points. 

DeAndre also dives into the Southwest Personal Cards and how earning 135,000 points can unlock the Southwest Companion Pass, offering free travel for a companion. Rounding out the episode, he touches on the Marriott Bonvoy Business card and its offer of five free nights with a spend requirement.

Get the key details fast and learn how to act quickly on these limited-time offers to maximize your travel rewards!

 

Key takeaways: 

  • The Chase Ink Business Unlimited card offers $900 cashback which is 90,000 points
  • You can convert cash back to travel points with certain cards.
  • Earning 135,000 points on Southwest Personal Cards grants the Companion Pass.
  • Timing is critical when applying for the Southwest Companion Pass.
  • The Marriott Bonvoy Business card offers five free nights after meeting the spending requirement.

 

Resources:

 

Connect with DeAndre Coke: 

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