travel
Point Me to First Class is a show for employed professionals, solopreneurs, entrepreneurs, and business owners with higher-than-average personal and/or business expenses who want to learn to leverage them into credit card points to spend on travel. Your expenses are your greatest untapped asset - but learning how to use them to travel the world doesn't have to be confusing or complicated. Each week, Devon Gimbel shares valuable tips, tools, and strategies to help you uplevel your skills earning and redeeming credit card points and shows you how to spend them on incredible travel experiences. Interested in learning more about working with Devon? Visit www.pointmetofirstclass.com to learn more. This podcast is for you if you find yourself asking questions like: How do I earn credit card points and use them for travel? How can I make my expenses benefit me? How can I earn as many credit card points for as little spending as possible? How to maximize value from credit card points. How to e
Avneesh Kohli, founder of SaveWise, revealed insights from indexing millions of shopping portal and card-linked offer data points over two and a half years. The analysis found that Capital One Offers ranks as the top shopping portal about 50% of the time, followed by cashback portal Top Cashback at around 41 to 42%, and Rakuten at 41%.
When analyzing airline-specific shopping portals, Avneesh Kohli shared that most airline portals generally trail behind general shopping portals, with a few exceptions. Surprisingly, the British Airways portal appeared in the top three rates about three times more often than any other airline shopping portal.
SaveWise data shows that shopping portal rates for top merchants change on average once every five days, with massive swings of 4x to 35x points. Furthermore, analyzing shopping behavior and alert triggers revealed that Mondays consistently offer rates about 24% better than baseline days, while weekends are the worst time to buy.
Comparing card-linked offers from major issuers, Avneesh Kohli noted that about 50% of Amex offers provide a return of 20% or more, compared to only about 1 in 7 Chase offers. However, lucrative Amex offers typically require higher spending thresholds, averaging around $240 to $250.
An analysis of 257 variations of direct Amex spending offers (earning Membership Rewards for meeting spend goals) revealed counterintuitive results. The best returns—nearly 2 membership rewards points per dollar spent—typically appear on lower-fee cards like Amex Everyday and Amex Green, rather than high-fee cards like Business Gold and Platinum.
Devin Gimbel and guest Katie discuss massive changes announced by Southwest Airlines to its Rapid Rewards loyalty program starting January 1st, 2027. The overhaul eliminates traditional methods of earning the coveted Companion Pass, such as welcome bonuses and shopping portals, replacing them with a requirement to achieve the highest elite status tier.
Katie explains that under Southwest's new loyalty program rules taking effect in 2027, travelers will need to accumulate 140,000 tier qualifying points primarily through $140,000 of direct credit card spending, as referral bonuses and welcome offers will no longer count.
Devin Gimbel and Katie discuss the remaining window in late 2026 where travelers can still earn a Companion Pass under old eligibility rules, noting that credit card applications must be approved by December 2nd to backdate points to the 2026 calendar year.
Devin Gimbel discusses how the American Express Personal Gold Card limits its four times points earning categories, capping grocery spend at $25,000 annually and worldwide restaurant spend at $50,000 annually.
Host Devin Gimbel explains that the mid-tier Built Obsidian card allows cardholders to choose either grocery or dining for three times points, but the grocery category is capped at $25,000 spent per calendar year.
Devin Gimbel points out that the Chase Freedom Flex and original Chase Freedom cards earn five times points on rotating quarterly categories, but restrict the bonus earnings to a strict limit of $1,500 total per card per quarter.
Devin Gimbel highlights a digital wallet promotion running through December 31, 2026, allowing multiple personal Chase cards to earn 10 times Chase points on up to $1,500 spent per month when using Pays at checkout.
Devin Gimbel warns business owners that the Chase Ink Business Cash Card earns five times points at office supply stores, but this bonus rate caps out at $25,000 per card member year on an anniversary schedule.
Maria Fung, founder of Maria Points the Way, argues that conventional advice on using transferable points for award travel, particularly for families aiming for business class to Asia, is often insufficient. She highlights that simply collecting popular points like Chase Ultimate Rewards may not be enough to secure premium cabin seats during peak travel periods.
Maria Fung shares her personal success in securing four business and first-class seats on ANA from San Francisco to Asia during winter break by shifting her strategy to focus on American Express (AMEX) points. She notes that ANA only partners with AMEX, making its points crucial for this specific redemption, despite having a large balance of Chase points.
Maria Fung points out a common misconception: limiting oneself to Chase partners for award travel might hinder booking opportunities, especially for popular routes to Asia. She specifically mentions EVA Air, a desirable airline for flights to Taipei, Thailand, and Australia, which partners with Capital One, HSBC, and City Bank, rather than Chase.
Maria Fung advises against relying exclusively on award search tools for finding flights on some Asian airlines, suggesting it can be a disadvantage. She advocates for learning manual award search techniques to uncover opportunities that automated tools might miss.
Devin Gimble, host of 'Point Me to First Class,' has developed a new tool called the Hidden Travel Budget Calculator. This calculator aims to help users estimate their potential points earnings from expenses and understand how much of that potential they are currently tapping into, providing a new way to gauge one's success in the points and miles hobby beyond just redemption value.
Devin Gimble argues that while redemption value is a calculable metric for points and miles, it's not the sole indicator of skill. He emphasizes that understanding and optimizing points earning potential from expenses is a more complex but crucial aspect of the hobby, offering significant untapped value for many users.
Devin Gimble explained that estimating points earning potential is highly individualized, depending on spending categories, targeted rewards cards, and overall credit card strategy. He contrasts a business owner with high travel expenses to a medical practice owner spending on supplies, highlighting how different spending patterns yield vastly different points-earning outcomes.
Devin Gimble's Hidden Travel Budget Calculator is designed with a conservative approach, focusing on the ongoing points earning from recurring expenses rather than solely on new card welcome bonuses. He believes that for many users, optimizing spending categories offers the most significant, yet often overlooked, potential for earning points.
Devin Gimble stressed that the Hidden Travel Budget Calculator is a personal tool, with no data storage or sharing capabilities. He explicitly stated that he does not see, save, or sell any user input, encouraging users to record any interesting results themselves for future reference.
James Berry, co-founder of Symphony, announced the launch of a new platform that allows users to earn transferable travel points or cash interest on their savings, aiming to disrupt the stagnant savings account industry. Symphony offers a fixed 5% APY, with users able to choose a customizable split between cash and points.
James Berry elaborated on Symphony's 5% APY, explaining that it's generated through a diversified portfolio including Treasury bills, private credit markets, and over-collateralized lending markets. Customer assets are held through broker-dealer custody relationships with Alpaca, which are covered by SPIC insurance, offering a different protection model than FDIC insurance.
James Berry highlighted that the savings industry has seen little innovation in decades, with traditional banks not incentivizing smart financial decisions for users. Symphony aims to be an alternative solution by making saving feel exciting and rewarding, aligning with the trend of younger generations seeking to take charge of their financial future.
Michelle and Devin discuss their recent stays at two Hyatt properties in Mexico, the Park Hyatt Cabo and Alila Maya Koba. They compare booking strategies, room types, and overall experiences to help listeners decide where to use their Hyatt points. Both guests highlight the value of Park Hyatt properties for point redemptions.
Michelle details her booking approach for the Alila Maya Koba, leveraging her Hyatt Globalist status and a category one through seven free night certificate for one night. The remaining three nights were booked with points, and she applied a suite upgrade award for additional space.
Devin explains his recurring need for warm weather escapes, particularly during winter breaks, to escape the "winter doldrums." He prioritizes resorts with good pools for his children and values Mexico as a convenient travel destination due to direct flights and similar time zones.
Michelle shares that her two-night stay at the Park Hyatt Cabo was redeemed at a rate of 40,000 points per night. While she did not use a suite upgrade award for this stay, she did reach out to the property in advance to note their anniversary celebration.
Steven Kimble introduces MileagePlus Upgrade Awards as a 'third option' for booking flights, distinct from paying cash or using miles for an outright award. This strategy involves booking a paid economy ticket and then using United miles along with a cash co-pay to confirm a seat in Polaris business class.
Miguel explains that MileagePlus Upgrade Awards are a "third path" to business class, blending cash and miles, and are often overlooked. He emphasizes that these awards are accessible to everyday travelers, not just those with elite status, as they can be secured using United miles without requiring Plus Points.
Steven Kimble notes that traditional award travel typically involves either paying cash or using points outright, with upgrades being complex and unpredictable. He highlights that United MileagePlus Upgrade Awards are less complicated and more accessible, even without elite status.
Miguel shares that his interest in MileagePlus Upgrade Awards stemmed from a desire to use fewer points when traveling with friends. Instead of booking an entire ticket for a friend with 80-100,000 points, he found it more efficient to use around 30,000 United miles for his friend, solving a problem of point redemption for group trips.
Miguel discusses using tools like seats.aero, specifically its 'United Plus Points Finder', to locate upgrade opportunities. He notes that while the tool is designed for elite members using Plus Points, it can also be used to find MileagePlus Upgrade Awards, which do not require elite status.