(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 163 of Points, Cards and Travel, Ross sits down with Kenny Hansen, founder and CEO of MentorPass, a platform connecting entrepreneurs with the mentors behind brands like Bloom Nutrition, Louis Vuitton, Native Deodorant, and Athletic Greens. Kenny shares how failing out of high school led him through community college to Virginia Tech and a six-year run at Accenture, before a trip to Bali changed everything. 

They dig into why he left a stable corporate job to build MentorPass overseas, why burnout doesn't seem to exist for the most successful people he's studied, and the "slow travel" system he and his fiancée now run their business on three-month stays, a dedicated office near a WeWork or Soho House, and a strict no-work-from-home rule. Ross also breaks down exactly which cards make sense for founders spending on Airbnbs and ad budgets, including how a $100K point haul turned into a $5,600 business class seat in Qatar. 

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

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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.

(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 162 of Points, Cards and Travel, Ross pulls back the curtain on his complete carry-on-only packing system, the one he's refined over 10+ years of travel, trial, error, and way too many "why did I even bring this" outfits. This week, Ross walks through exactly how he and his wife packed for a full 17-day honeymoon using nothing but a carry-on and a backpack each, no checked bags required.

You'll hear his real product recommendations for carry-on luggage, why packing cubes are a total game-changer, the 3-shoe rule that covers literally any trip, and the small but mighty extras (sleep mask, portable charger, AirTags, international adapters) that quietly save every trip from disaster. By the end, he breaks down all 45 items he packs and exactly how they all fit into one bag.

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

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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.

(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 161 of Points, Cards and Travel, Ross sits down with Betsy Wilson, founder of Become Travel Rich and widely known in the points and miles community as the go-to expert on all things Alaska Airlines. Betsy breaks down the new 100,000-point sign-up bonus on the Atmos Summit card (better known as the "Alaska Black Card"), the real difference between the cash companion fare and the companion award certificate, and how American Airlines elites already get reciprocal status on Alaska flights. 

They also cover underrated sweet spots, like 35,000 points and $6 for a domestic lie-flat business class seat, and a 55,000-point business class run from Anchorage to Frankfurt on Condor, plus how to stack non-airline partners like 1-800-Flowers and Guaranteed Rate for extra points. To close it out, Betsy maps out exactly how to spend 10 to 12 days exploring Alaska itself, from Anchorage's museums to the fishing town of Homer. If you've ever wondered how to make the most of Alaska Airlines' loyalty program, or just need a reason to finally visit Alaska, this episode is for you. 

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

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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.

(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 160 of Points, Cards and Travel, Ross continues the Points and Miles credit card series by tackling the question he gets asked the most: are annual fees actually worth it? He breaks it down into five buckets, free night certificates, lounge access and premium services, monthly and quarterly statement credits, points accelerators, and built-in protections like travel insurance and walks through real, personal examples for each. 

That includes how a $99 IHG Premier Rewards Card turned into five free nights worth over $3,500 in savings (used on a Bangkok honeymoon and a Grand Cayman stay), how the Capital One Venture X's $395 fee was wiped out before a single point was earned, and how the American Express Platinum's $695 fee gets offset by hundreds of dollars in monthly credits most people forget to activate. Ross also covers the World of Hyatt card's category 1-4 free night, the Hilton Honors Aspire's Lyft Pink Plus perk, and why he'd never recommend stacking two premium cards with overlapping benefits. Whether you're annual-fee-curious or already deep into the points game, this episode reframes the math: an annual fee isn't a cost, it's an upfront investment. 

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

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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.

(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 159 of Points, Cards and Travel, Matt Dong, co-founder of Wuhoo Group, joins Ross to break down how Star Alliance transfer partners turn an average United flight into a fraction of the points. Matt has stayed at over $40,000 worth of Hyatt nights for $0, and recently flew a trip that would've cost nearly $44,000 in cash for just $356. 

The conversation centers on Dulles as a Star Alliance hub, why transferring Chase, Amex, and Capital One points to Air Canada almost always beats booking United directly, and how a Houston flight dropped from 40,000 points to 15,000 just by changing where you transfer. Matt also shares the lap infant mistake that cost him $2,200 on a flight to Hong Kong, the accounts you should open now before you ever need them, and why the Capital One Venture X is his go-to recommendation for anyone flying out of Dulles or DCA. Whether you're planning your first trip to Paris or chasing your fifth Star Alliance business class seat, this episode is the roadmap. 

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

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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.

(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 158 of Points, Cards and Travel, Ross continues the Points and Miles credit card series by breaking down exactly how to turn transferable points into business class flights instead of cash. He compares booking through the Capital One travel portal, where cards like the Venture Rewards and Venture X earn 5x to 10x points on flights, hotels, and rental cars, against transferring points directly to airline loyalty programs for outsized value. Using real examples from his own bookings. 

Ross shows how 200,000 Capital One points became two business class seats from Charlotte and Atlanta to Bangkok worth over $11,350 through British Airways and the Oneworld alliance, how 12,000 miles covered a $250 flight to Northern Virginia on Etihad, and how transfer bonuses from Qantas and British Airways turned smaller point balances into hundreds of dollars in savings on flights to Ohio and Grand Cayman. He also revisits the cardinal rules from last week's episode: never redeem for gift cards, cash, or statement credit, and never transfer points speculatively without confirming seat availability first. 

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

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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.

(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 157 of Points, Cards and Travel, Ross sits down with Ben from Ben's Big Deals to go deep on everything about hotels: the strategies, the mistakes, and the redemptions that actually move the needle. Ben got his start as a business traveler discovering La Quinta Inn loyalty perks, a "vacation" his wife was not impressed by, and that early lesson shapes everything he teaches today. They cover why emailing a property before you arrive (and telling them why you're there) can unlock complimentary upgrades, why talking to a manager beats the front desk, and why shorter stays make upgrades easier to land. 

Ben breaks down his points pyramid (bank points, then airlines, then hotels), why Hyatt and Accor are the exceptions to weak hotel point values, and why the Hilton free night certificate might be the single most valuable certificate in travel. They also get into aspirational stays worth chasing on points, including Alila Ventana in Big Sur and Hyatt's wellness brand Miraval, soon opening its first international property on the Red Sea. Ben closes with what's inside his Hotel Masterclass. 

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

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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.

(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 156 of Points, Cards and Travel, Ross walks through the ultimate pre-trip planning and vacation document checklist, the exact system he's refined over 10+ years of travel mistakes so you don't have to repeat them. Before diving into documents, Ross covers the planning fundamentals: figuring out your travel style, setting up flight alerts through Google Flights, Skyscanner, or the Capital One travel portal, and choosing the right apps to manage your itinerary (Google Docs, Google Maps, TripIt, Viator, and more).

From there, he breaks down the full document checklist for any trip, domestic or international, including visas and vaccinations, backup flight and accommodation confirmations, travel insurance (and which credit card benefits actually cover it), car rental and tour ticket downloads, emergency contacts, and passport copies. Ross also shares his cash and currency strategy for avoiding hidden transaction fees abroad, plus why splitting your cards, cash, and IDs across bags can save a trip when something goes wrong. If you want all of this compiled for you, Ross's free Stress-Free Travel Starter Kit has the entire checklist ready to go. Next week: the vacation packing checklist.

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

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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.

(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 154 of Points, Cards and Travel, Ross sits down with Leslie Douglas, VP of Sales at Sell Better, sales trainer, podcast host, and self-described "Delta girly and Marriott girly." Leslie shares how she balances life on the road (30-40% travel) as a mom while building a points strategy that's covered nearly free trips, including an $80 all-in trip to New York with her daughter. The conversation dives into business expense strategies, including Leslie's story of putting a $10,000 car down payment on her American Express card for instant elite status, why every reimbursable expense should go on your personal card, and how recurring business costs can be converted into travel rewards. 

They also cover tools like Card Pointers Pro and Rakuten for stacking offers, the importance of picking an airline/hotel "home base," and simple money habits like automated high-yield savings accounts for funding future trips. Whether you're a sales rep, business owner, or frequent traveler with kids, this episode is packed with practical, real-world strategies for traveling more without spending more. 

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

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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.

(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 154 of Points, Cards and Travel, most business owners avoid credit cards for vendor payments because of the 3% processing fee, but that mindset could be costing them millions of points. In this episode, Ross breaks down how tools like Plastiq and Melio let you pay contractors, vendors, and service providers who only accept cash or check using a credit card, unlocking massive points-earning potential. 

Ross walks through real numbers: a $580,000 annual spend turning into $46,000+ of travel value, and how scaling to 3-5x multipliers can push that even higher. Whether you're a real estate investor, house flipper, or business owner working with old-school vendors, this episode shows you how a simple two-card stack and the right software can transform routine expenses into life-changing travel 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

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