Tag: Travel Rewards

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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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[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:

 

Interested in Financial Planning?

 

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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:

 

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 Matt Jamele:

 

 

 

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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:

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 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:

 

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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How Business (and Life) Partners Can Turn Shared Expenses Into Luxury Travel with Dr. Andrea Mabry (Ep. 70)

How Business (and Life) Partners Can Turn Shared Expenses Into Luxury Travel with Dr. Andrea Mabry (Ep. 70)

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Can you build a business and a travel lifestyle at the same time?

 In this episode of Revolutionizing Your Journey, dermatologist and entrepreneur Andrea Mabry joins host DeAndre Coke to reveal how she leveraged high-value business expenses to earn millions of points and miles. From negotiating with contractors on a multi-million dollar clinic build to strategically choosing between Chase, Capital One, and Amex cards, Andrea shares actionable tips for entrepreneurs looking to turn their business spend into unforgettable travel rewards. They dive deep into the pros and cons of sharing points with partners, the surprising differences between credit card issuers, and how Andrea used AI to decide between points and cash back. You’ll also hear about her family’s premium cabin redemptions, the true value of understanding credit card fine print, and how setting aside just one hour can lead to long-term rewards.

 If you’re a business owner or aspiring entrepreneur looking to maximize every dollar—this one’s for you.

 

Key Highlights:

  • Business Expense Strategy: Andrea used business spending, including building a clinic, to earn over 700,000 points annually.
  • Credit Card Comparison: Chase offers substantial rewards but is hard to share; Capital One is the most flexible for transfers.
  • Amex Point Tracking: Requires manual systems to manage partner point splits effectively.
  • Contractor Negotiation: Paying large vendors with cards led to significant point accumulation.
  • Cash Back vs Points: Andrea used AI tools to compare long-term value and determine the best strategy.
  • Family Travel: Thanks to effective redemption planning, she flew seven family members in premium cabins.
  • Quick Setup: Setting up a points system can take less than an hour but deliver massive returns.
  • Teaching Others: Andrea educates her network to create shared travel opportunities.
  • Redemption Stories: From Thailand to Iceland, points have become unforgettable travel memories.

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 Andrea Mabry:

 

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Quick Hits: More Zil Payroll Woes and More!

Quick Hits: More Zil Payroll Woes and More!

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In this Quick Hits episode, DeAndre Coke checks in from the stunning Park Hyatt Beaver Creek in Colorado, offering a glimpse into the luxury ski-in/ski-out experience. 

He shares the latest on the ongoing Zil Money payroll issues, including frustrations from users unable to process payments via credit card. The episode also covers recent turbulence with Southwest Airlines, from point devaluations to new passenger fees, and how American and Delta are stepping in with status match opportunities. DeAndre closes out by breaking down the new Chase and United card changes, which have sparked conversations around value, fees, and whether these cards still make sense for savvy travelers.

Whether you’re navigating the slopes of travel rewards or reassessing your credit card strategy, this episode delivers timely insights to help you make smarter moves with your points and miles.

 

Key takeaways: 

  • Park Hyatt Beaver Creek: A true ski-in/ski-out luxury resort offering a premium travel experience.
  • Zil Money Update: The payroll-by-card system experienced downtime, impacting users across multiple platforms.
  • Southwest Airlines Devaluation: Points were devalued, and new fees were introduced, frustrating loyal customers.
  • Status Match Opportunities: American Airlines and Delta are offering matches for Southwest elites.
  • Chase & United Card Changes: Increased annual fees and reduced perks make co-branded cards less valuable.
  • Community Insight: Ongoing discussions in the Boldly Go Facebook group reflect traveler concerns and strategies.
  • Rewards Program Monitoring: Staying informed is key to adapting to the changing travel rewards landscape.

 

Resources:

 

Connect with DeAndre Coke: 

 

 

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Unlocking the Secrets of American Airlines Loyalty Rewards with @allieandlandon (Ep. 68)

Unlocking the Secrets of American Airlines Loyalty Rewards with @allieandlandon (Ep. 68)

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How can you earn airline status without even setting foot on a plane? 

In this episode of the Revolutionizing Your Journey podcast, host DeAndre Coke sits down with Allie Ruhde, aka @allieandlandon—an expert in travel rewards and American Airlines’ loyalty system—to unpack precisely that. Allie shares her journey into the world of points and miles, starting with earning Gold status at just three years old. Together, they dive deep into the mechanics of American Airlines’ Loyalty Points system, including strategies for earning status through shopping portals, dining programs, hotel bookings, and credit cards.

The conversation also explores the perks of status levels like Platinum, Platinum Pro, and Executive Platinum, lounge access options, and how to maximize your everyday spending to unlock travel rewards. Plus, Allie explains why Alaska Airlines stands out in the OneWorld alliance and shares her favorite redemption tips—like flying to Japan in business class for just 60,000 miles. Whether you’re a seasoned traveler or just starting your loyalty journey, this episode is packed with practical insights you can apply right away.

 Tune in to learn how to stack miles and Loyalty Points smarter—not harder.

 

Key Highlights:

  • Loyalty Points 101: Track status progress without needing to fly.
  • Shopping Portals: A powerful way to rack up Loyalty Points and miles.
  • Dining Rewards: Earn miles for everyday meals with linked credit cards.
  • Hotel Bookings: Book through AA Hotels to earn high Loyalty Points.
  • Status Tiers: Platinum and Executive Platinum bring valuable perks like upgrades and lounge access.
  • Alaska Airlines: Offers complimentary upgrades—unlike other OneWorld airlines.
  • Credit Cards: AA co-branded cards earn both Loyalty Points and miles.
  • Upgrade Strategy: Maximize same-day change policies and early boarding.
  • Pro Tips: Combine Simply Miles offers, use status challenges wisely, and don’t overlook dining and shopping portals.

 

Resources:

 

Connect with DeAndre Coke: 

 

Connect with Allie Ruhde:

 

 

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