Month: May 2025

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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:

 

CPA’s Footnotes:

 

Connect with DeAndre Coke: 

 

Connect with Rachel Earl:

 

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[YouTube Bonus] How I Stayed at a $7,500 Ski Resort for FREE Using Points | Park Hyatt Beaver Creek Review

[YouTube Bonus] How I Stayed at a $7,500 Ski Resort for FREE Using Points | Park Hyatt Beaver Creek Review

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Can you enjoy a luxury ski trip for almost free? 

In this episode, DeAndre Coke shares his four-night stay at the 5-star Park Hyatt Beaver Creek in Colorado—paid entirely with points and miles. This trip had everything from a suite upgrade and gourmet breakfasts to ski-in, ski-out access and firepit s’mores. 

Tune in to hear how DeAndre booked the stay, tips for maximizing your points, and what to expect from one of Colorado’s most family-friendly mountain resorts.

 

Resources:

 

Connect with DeAndre Coke: 

 

 

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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:

 

Connect with DeAndre Coke: 

 

 

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From Gigs to Getaways: How Musicians Can Travel Smarter Using Points & Miles with @miles_maestro (Ep. 74)

From Gigs to Getaways: How Musicians Can Travel Smarter Using Points & Miles with @miles_maestro (Ep. 74)

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How can musicians and creatives take advantage of points and miles to make travel more affordable—and more meaningful?

In this episode of Revolutionizing Your Journey, host DeAndre Coke chats with musician and points enthusiast Matt Jamele, better known as @miles_maestro, about the travel challenges artists face and the strategies that can make the road a little smoother.

Matt shares how his desire to travel more—despite the financial unpredictability of being an artist—led him to the world of points and miles. From choosing the right credit cards and maximizing free night certificates to creating unforgettable moments on the road, he offers practical advice for creatives who want to stretch their travel budgets. The conversation touches on lounge access, business card perks, and how to keep things simple while still traveling well. If you’re touring across the country or planning a well-deserved getaway between gigs, this episode will inspire you to rethink your travel as an artist.

 

Key Highlights:

  • Matt’s beginnings: His passion for travel grew while navigating the financial realities of being a working musician.
  • Business card benefits: A business credit card can offer valuable rewards for artists with side income.
  • Lounge access perks: Airport lounges provide much-needed comfort between gigs or flights.
  • Simple card strategy: A lean card setup is often more manageable and effective for creatives.
  • Redemption value: Points can be used for experiences that create lasting memories, not just luxury.
  • Ask for help: There’s a growing community of travel hackers willing to guide beginners.
  • Travel mindset: The focus should be on enjoying the journey, not overcomplicating it with dozens of strategies.
  • Accessible travel: With a bit of planning, even independent artists can explore the world without overspending.

 

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

 

Resources:

 

Connect with DeAndre Coke: 

 

Connect with Matt Jamele:

 

 

 

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Quick Hits: Real ID Is Finaly Here, 2 Top Credit Card Offers Are Ending Soon & More!

Quick Hits: Real ID Is Finaly Here, 2 Top Credit Card Offers Are Ending Soon & More!

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How do you stay updated with travel news while soaking up the sun in paradise? In this Quick Hits episode, DeAndre Coke checks in from the beautiful Kimpton Grand Roatán Resort in Honduras, where he shares a snapshot of the latest travel and points and miles updates.

He covers the current round of valuable transfer bonuses from Capital One, Chase, Citi, and more—along with timely reminders like the launch of REAL ID requirements in the U.S. and major airport delays affecting travel through New York and New Jersey. He also includes two major credit card welcome offers, including the $1,000+ value Capital One Venture Rewards deal ending May 12th.

If you’re booking a summer getaway or optimizing your rewards portfolio, this episode will help you make smart, timely moves with your travel plans.

 

Key takeaways: 

  • Current Transfer Bonuses: Capital One, Chase, and Citi are offering bonuses up to 30%—ideal if you’re booking travel soon.
  • REAL ID Reminder: Domestic travelers without a REAL ID-compliant license must carry a passport for flights.
  • Northeast Flight Disruptions: Avoid flights through New York/New Jersey due to air traffic staffing issues and cancellations.
  • Chase Sapphire Preferred: The 100K point sign-up bonus is in the “last call” phase—if you’re eligible, don’t miss it.
  • Capital One Venture Offer: Earn 75K miles + $250 travel credit (worth $1,000+) if you apply by May 12.
  • Travel Tip from Honduras: The Kimpton Grand Roatán is a stunning destination spa—watch for a full breakdown episode soon.

 

Resources:

 

Connect with DeAndre Coke: 

 

 

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Travel Smarter with Joy & Mara of @savvytravelmamas: Points, Timeshares & Travel Freebies (Ep. 73)

Travel Smarter with Joy & Mara of @savvytravelmamas: Points, Timeshares & Travel Freebies (Ep. 73)

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Can vacation clubs and timeshares be worth it, and how do you avoid the traps?

 In this episode of Revolutionizing Your Journey, host DeAndre Coke welcomes Joy Smith and Mara Rice, better known as the Savvy Travel Mamas, for a candid conversation on travel strategies, points and miles, and making family vacations a reality without breaking the bank. Mara shares how she started travel hacking decades ago out of financial necessity. At the same time, Joy reflects on her evolution from avoiding travel planning to becoming the go-to organizer for unforgettable getaways.

They break down the difference between vacation clubs and timeshares, discuss how to spot (and avoid) high-pressure sales tactics—especially in Las Vegas—and explain why freebies can be both a perk and a pitfall. You’ll also hear personal stories from their stays at Hilton and Hyatt resorts, tips for using credit cards wisely, and prioritizing experiences without overspending. This episode offers a practical guide for families, beginners, and anyone curious about getting more from their travels through smart planning and intentional choices.

 

Key Highlights:

  • Mara’s beginnings: She started using points and miles out of necessity, proving you don’t need money to travel smart.
  • Joy’s shift: Initially hesitant, Joy embraced travel planning to prioritize family vacations.
  • Vacation club clarity: Understanding the structure of vacation clubs vs. timeshares is critical to making wise decisions.
  • Maximizing redemptions: Spacious accommodations and points strategy make family travel more affordable.
  • Common mistakes: Many people jump into timeshares without understanding what they buy.
  • Financial insight: Being financially responsible when considering ownership is key.
  • Presentation strategy: If you prepare, you can attend sales presentations just for the perks.
  • Vegas freebies: Joy and Mara reveal how they scored thousands in vacation value just by showing up.
  • Family-first mindset: Travel should work around your family’s needs, not the other way around.
  • Start small: You don’t have to jump into luxury travel—start where you are and build from there.

 

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

Resources:

 

Connect with DeAndre Coke: 

 

Connect with savvytravelmamas:

 

 

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Quick Hits: Chase & Amex Pause Emirates Transfers, The Zil Money Payroll Saga Continues and More!

Quick Hits: Chase & Amex Pause Emirates Transfers, The Zil Money Payroll Saga Continues and More!

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Is travel finally getting cheaper again? In this Quick Hits episode, DeAndre Coke breaks down the latest shifts in travel trends, including a noticeable drop in flight prices and increased award seat availability, especially in business and first class. He explains why now might be the ideal time to snag flight deals using points or cash and shares valuable tools for smarter travel booking, including the newly launched hotel search tool Gondola.

DeAndre also provides an update on the ongoing saga of using payroll for your credit cards with Zil Money, which has been down for over a month now. He also covers a fast-closing loophole that lets travelers transfer Amex points to Alaska Airlines miles. He warns listeners about the upcoming temporary suspension of point transfers from Chase and Amex to Emirates. The episode closes with a heads-up on an active 30% transfer bonus from Citi ThankYou Rewards to Virgin Atlantic Flying Club, along with key considerations for making the most of those points.

From smart booking strategies to maximizing redemptions, this update helps you make the most of the current travel climate.

 

Key takeaways: 

  • Flight Prices Dropping: Demand is cooling, bringing cheaper cash fares and improved award availability.
  • Alaska Airlines Loophole: The Amex → Hawaiian → Alaska transfer hack may end soon—act fast.
  • Gondola Tool: A new site showing cash vs. points hotel prices, elite benefits, and price tracking, though it requires email read access.
  • Emirates Transfers Paused: Chase (May 28–June 30) and Amex (starting May 29) are temporarily pausing point transfers to Emirates, hinting at a likely devaluation.
  • Virgin Atlantic Transfer Bonus: 30% bonus on Citi ThankYou Rewards transfers to Virgin Atlantic Flying Club through May 17.
  • Thrifty Traveler & Daily Drop: Helpful tools for spotting mistake fares and daily point deals.
  • Cash vs Points Strategy: When flight prices drop, cash may offer better value than points. 

 

Resources:

 

Connect with DeAndre Coke: 

 

 

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