The BoldlyGo Podcast: Revolutionizing Your Journey

In this value-packed Quick Hits episode, DeAndre Coke breaks down the most significant developments in the points and miles world—from exciting transfer bonuses and premium card promos to major airline pricing changes and credit card legislation that could impact your travel rewards. He highlights Thrifty Traveler’s limited-time 50% off deal, an elevated IHG card bonus offering 5 free nights, new baggage fees from Southwest, and a game-changing partnership between United and JetBlue.

DeAndre also shares updates on Amex, Chase, and Citi transfer bonuses, the Capital One lounge guest access shake-up, and the growing concern over the Credit Card Competition Act. Whether you’re just getting started with points or already planning your next redemption, there’s something in this episode for you. Listeners are also reminded to take advantage of free strategy consultations to get personalized travel game plans.

Key takeaways: 

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: 

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:

• Book a Free 30 minute points & miles consultation
• Start here to learn how to unlock nearly free travel
• Sign up for our newsletter!
• This month’s best current card offers
• BoldlyGo Travel With Points & Miles Facebook Group

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

Note: Contains affiliate/sponsored links

• Card Pointers (Saves the average user $750 per year)
• Zil Money (For Payroll on Credit Card)
• Travel Freely
• Point.me
• FlightConnections.com
• Thrifty Traveler Premium
• LTH Online Points & Miles In Depth Course: Use coupon code “BOLDYGO” for a 50% discount!

Connect with DeAndre Coke:

• Instagram: BoldlyGo.world
• TikTok: BoldlyGo.world
• Website: BoldlyGo.world
• YouTube: BoldlyGoWorld
• YouTube: BoldlyGo.Travels

In this YouTube bonus episode of Revolutionizing Your Journey, DeAndre Coke recaps his recent all-cash stay at The Estate Yountville, a luxury resort in the heart of Napa Valley. From the moment of arrival—greeted with wine and surrounded by tree-lined serenity—to the property’s 24-hour pool, fire pits, and high-end amenities, DeAndre offers a full breakdown of what makes this resort both elegant and approachable. He explores the walkability of Yountville’s top tasting rooms, the thoughtful touches like complimentary town cars, and the experience of traveling with fellow financial advisors. The episode wraps with DeAndre’s honest take on the value of the stay and tips on how to recreate similar trips using points and miles for a fraction of the price.

Resources:

• YouTube vlog The Estate Yountville Review
• Start here to learn how to unlock nearly free travel
• Sign up for our newsletter!
• LTH Online Points & Miles In Depth Course: Use coupon code “BOLDYGO” for a 50% discount!
• BoldlyGo Travel With Points & Miles Facebook Group

Connect with DeAndre Coke:

• Instagram: BoldlyGo.world
• TikTok: BoldlyGo.world
• Website: BoldlyGo.world
• YouTube: BoldlyGoWorld
• YouTube: BoldlyGo.Travels

Looking to stay ahead in the world of travel rewards?

In this week’s Quick Hits episode of Revolutionizing Your Journey, host DeAndre Coke delivers a rapid roundup of the most essential travel news and deals you need to know right now. From a 50% discount on Thrifty Traveler Premium to a Clear membership price hike, quirky hotel promotions, and the end of an iconic round-the-world points redemption, this episode is packed with timely tips. DeAndre also highlights how travelers can stay connected to the community and where to take action quickly to unlock significant value.

If you’re trying to maximize every dollar and point this season, this is one to catch.

Key takeaways:

• 50% Off Thrifty Traveler Premium: New subscribers can join for just $50 from June 4–9. Great for finding rare points and cash deals.
• Clear Membership Price Hike: The annual fee is now $199. Still worth it if your card covers the cost—less so if you’re paying out-of-pocket.
• Kimpton’s Secret Password Is Back: Say “Social Sent Me” at check-in for surprise perks like snacks, upgrades, or waived fees (through Aug 31).
• ANA Round-the-World Ticket Ending: Book by June 24 to snag this legendary 105k-point deal with 12 segments and 8 stopovers.

Resources:

• Book a Free 30 minute points & miles consultation
• Start here to learn how to unlock nearly free travel
• Sign up for our newsletter!
• This month’s best current card offers
• BoldlyGo Travel With Points & Miles Facebook Group

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

Note: Contains affiliate/sponsored links

• Card Pointers (Saves the average user $750 per year)
• Zil Money (For Payroll on Credit Card)
• Travel Freely
• Point.me
• FlightConnections.com
• Thrifty Traveler Premium
• LTH Online Points & Miles In Depth Course: Use coupon code “BOLDYGO” for a 50% discount!

Connect with DeAndre Coke:

• Instagram: BoldlyGo.world
• TikTok: BoldlyGo.world
• Website: BoldlyGo.world
• YouTube: BoldlyGoWorld
• YouTube: BoldlyGo.Travels

Planning a Disney trip and want to save big without sacrificing comfort?

In this episode of Revolutionizing Your Journey, host DeAndre Coke sits down with Chelsea from Pixie Point Gals to uncover the real magic behind using the Disney Vacation Club (DVC) and travel points to experience Disney like never before. Chelsea breaks down how families can rent DVC points—even without a membership—and stay at deluxe Disney resorts for a fraction of the price. They talk about the perks of staying on-property, tips for adults visiting Disney, and clever hacks like relocating food between resorts.

From avoiding scams to maximizing credit card points, this episode is packed with practical advice and insider tricks for both Disney lovers and travel hackers alike.

Key Highlights:

• DVC explained: The Disney Vacation Club operates on a point system that differs from traditional timeshares.
• Renting advantage: Renting DVC points can save up to 50% on high-end resort stays—even for non-members.
• Booking flexibility: Being open to travel dates and resorts helps unlock better deals and availability.
• Adult Disney tips: High-end resorts like the Riviera and experiences like Epcot’s “drink around the world” cater to adults.
• On-property perks: Early park entry, free transportation, and deluxe amenities make staying on-site worthwhile.
• Points strategy: Combining DVC rentals with travel credit card points furthers savings.
• Avoiding scams: Booking through verified DVC rental sites helps ensure a smooth and secure experience.
• Enhancing the trip: Small tricks like having Disney relocate luggage (and even food) between resorts can elevate the magic.

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

Resources:

• Book a Free 30 minute points & miles consultation
• Start here to learn how to unlock nearly free travel
• Sign up for our newsletter!
• This month’s best current card offers
• BoldlyGo Travel With Points & Miles Facebook Group

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

Note: Contains affiliate/sponsored links

• Card Pointers (Saves the average user $750 per year)
• Zil Money (For Payroll on Credit Card)
• Travel Freely
• Point.me
• FlightConnections.com
• Thrifty Traveler Premium
• LTH Online Points & Miles In Depth Course: Use coupon code “BOLDYGO” for a 50% discount!

Connect with DeAndre Coke:

• Instagram: BoldlyGo.world
• TikTok: BoldlyGo.world
• Website: BoldlyGo.world
• YouTube: BoldlyGoWorld
• YouTube: BoldlyGo.Travels

Connect with Pixie Point Gals:

• Instagram: pixiepointgals
• Website: pixiepointgals.com

Looking to maximize your points game and stay ahead of the travel curve?

In this extended Quick Hits episode, DeAndre Coke dives into one of the busiest travel news weeks yet. From Rakuten and SoFi points play to Delta’s award rate drops and United’s sleek new Polaris business class suites, there’s something for every traveler. He covers the Hilton Honors devaluation, a limited-time AA award sale, and the end of the valuable Amex-to-Hawaiian-to-Alaska Airlines transfer loophole. Plus, there’s new info on Chase’s Instacart perks, updates on the Zil Money saga, and a reminder that May is prime time for booking summer travel.

Packed with strategy, news, and savings hacks—you won’t want to miss it.

Key takeaways:

• Rakuten deals: Huge Amex point earning opportunities—some merchants offering up to 95x points.
• SoFi bonus: Opening a new SoFi account with a $500 direct deposit can earn 25,000 Amex points.
• Delta award rates drop: Flying Blue redemptions on Delta-operated flights are ~20% cheaper for 2026.
• United upgrades: New Polaris Studio Suites will offer luxury in-flight experiences starting in 2026.
• Hilton devaluation: Standard award nights at top-tier hotels now cost up to 200,000 points.
• American Airlines sale: Over 1 million award seats available from 5,000 miles—book by May 28.
• Amex transfer loophole: The Amex-to-Hawaiian-to-Alaska points route ends June 30.
• Chase Instacart perks: New $10–$20 monthly credits across many cards, plus free Instacart+ trials.
• Zil Money update: The payroll on credit card feature was delayed another month, which is now expected in June.
• Book now for summer: Prices for flights and hotels are lower than usual—rebooking could save $$$.

Resources:

• Rakuten Referral Link
• Shopping Portals Explained (Ep. 49)
• Blog: How to Use Shopping Portals to Boost Your Points and Miles
• Start here to learn how to unlock nearly free travel
• Sign up for our newsletter!
• This month’s best current card offers
• LTH Online Points & Miles In Depth Course: Use coupon code “BOLDYGO” for a 50% discount!
• BoldlyGo Travel With Points & Miles Facebook Group
• Thrifty Traveler Premium
• Daily Drop Newsletter
• Book a Free 30 minute points & miles consultation
• This month’s best current card offers
• BoldlyGo Travel With Points & Miles Facebook Group

Interested in Financial Planning?

• Truicity Wealth Management

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

Note: Contains affiliate/sponsored links

• Card Pointers (Saves the average user $750 per year)
• Zil Money (For Payroll on Credit Card)
• Travel Freely
• Point.me
• FlightConnections.com
• Thrifty Traveler Premium
• LTH Online Points & Miles In Depth Course: Use coupon code “BOLDYGO” for a 50% discount!

Connect with DeAndre Coke:

• Instagram: BoldlyGo.world
• Website: BoldlyGo.world
• YouTube: BoldlyGoWorld

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:

• Book a Free 30 minute points & miles consultation
• Start here to learn how to unlock nearly free travel
• Sign up for our newsletter!
• This month’s best current card offers
• BoldlyGo Travel With Points & Miles Facebook Group

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

Note: Contains affiliate/sponsored links

• Card Pointers (Saves the average user $750 per year)
• Zil Money (For Payroll on Credit Card)
• Travel Freely
• Point.me
• FlightConnections.com
• Thrifty Traveler Premium
• LTH Online Points & Miles In Depth Course: Use coupon code “BOLDYGO” for a 50% discount!

CPA’s Footnotes:

• https://www.irs.gov/pub/irs-drop/a-02-18.pdf
• https://www.thetaxadviser.com/issues/2021/may/credit-card-rewards-purchases-gift-cards/ (Interesting Tax Court case about how a couple redeemed points and what the Court considered taxable income)
• https://www.irs.gov/pub/irs-wd/202417021.pdf (This is for those who want to get really nerdy about tax and points)
• https://www.irs.gov/newsroom/questions-and-answers-on-the-net-investment-income-tax (Resource for those that may want to know more about Net Investment Income Tax)

Connect with DeAndre Coke:

• Instagram: BoldlyGo.world
• TikTok: BoldlyGo.world
• Website: BoldlyGo.world
• YouTube: BoldlyGoWorld
• YouTube: BoldlyGo.Travels

Connect with Rachel Earl:

• Instagram: viachoremtax

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:

• Book a Free 30 minute points & miles consultation
• Start here to learn how to unlock nearly free travel
• Sign up for our newsletter!
• This month’s best current card offers
• BoldlyGo Travel With Points & Miles Facebook Group

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

Note: Contains affiliate/sponsored links

• Card Pointers (Saves the average user $750 per year)
• Zil Money (For Payroll on Credit Card)
• Travel Freely
• Point.me
• FlightConnections.com
• Thrifty Traveler Premium
• LTH Online Points & Miles In Depth Course: Use coupon code “BOLDYGO” for a 50% discount!

Connect with DeAndre Coke:

• Instagram: BoldlyGo.world
• Website: BoldlyGo.world
• YouTube: BoldlyGoWorld

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:

• Rakuten Promo: Get a 7,500 point bonus after you spend $25
• Shopping Portals Explained (Ep. 49)
• Blog: How to Use Shopping Portals to Boost Your Points and Miles
• Start here to learn how to unlock nearly free travel
• Sign up for our newsletter!
• This month’s best current card offers
• LTH Online Points & Miles In Depth Course: Use coupon code “BOLDYGO” for a 50% discount!
• BoldlyGo Travel With Points & Miles Facebook Group
• Thrifty Traveler Premium
• Daily Drop Newsletter
• This month’s best current card offers
• BoldlyGo Travel With Points & Miles Facebook Group

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

Note: Contains affiliate/sponsored links

• Card Pointers (Saves the average user $750 per year)
• Zil Money (For Payroll on Credit Card)
• Travel Freely
• Point.me
• FlightConnections.com
• Thrifty Traveler Premium
• LTH Online Points & Miles In Depth Course: Use coupon code “BOLDYGO” for a 50% discount!

Connect with DeAndre Coke:

• Instagram: BoldlyGo.world
• Website: BoldlyGo.world
• YouTube: BoldlyGoWorld

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:

• Book a Free 30 minute points & miles consultation
• Start here to learn how to unlock nearly free travel
• Sign up for our newsletter!
• This month’s best current card offers
• BoldlyGo Travel With Points & Miles Facebook Group

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

Note: Contains affiliate/sponsored links

• Card Pointers (Saves the average user $750 per year)
• Zil Money (For Payroll on Credit Card)
• Travel Freely
• Point.me
• FlightConnections.com
• Thrifty Traveler Premium
• LTH Online Points & Miles In Depth Course: Use coupon code “BOLDYGO” for a 50% discount!

Connect with DeAndre Coke:

• Instagram: BoldlyGo.world
• Website: BoldlyGo.world
• YouTube: BoldlyGoWorld

Connect with Matt Jamele:

• Instagram: miles_maestro