Podcast Summary: All the Hacks with Chris Hutchins
Episode: The Path to Becoming an Expert in Points & Miles with Devon Gimbel
Release Date: May 14, 2025

Introduction

In this enlightening episode of "All the Hacks with Chris Hutchins," host Chris Hutchins welcomes Devon Gimbel, a seasoned expert in the Points and Miles (P&M) space. The duo delves deep into Devon's unique four-step framework for mastering P&M, offering listeners both novices and seasoned enthusiasts invaluable strategies to optimize their rewards for travel and beyond.

Understanding Points & Miles Differently

Devon Gimbel begins by distinguishing her approach from conventional P&M strategies. Instead of merely focusing on minimizing travel costs, she emphasizes "how can I take this travel budget that I've allocated, how can I expand it exponentially using points" (02:37). This shift in perspective allows for greater flexibility and maximizes the personal value derived from points and miles.

She critiques mainstream advice that often revolves around "always working on a new welcome bonus offer" and allocating all expenses to new credit cards. Devon shares her experience of scaling back on this method due to the impracticality of managing numerous credit cards as her and her husband's businesses grew, leading to increased expenses (02:37).

The Dunning-Kruger Effect in Points & Miles

The conversation transitions into the Dunning-Kruger Curve, a psychological model explaining how individuals perceive their competence relative to their actual knowledge (04:56). Devon likens the initial confidence many P&M enthusiasts feel despite limited knowledge to the "peak of Mount Ignorance." As learners gain more information, their confidence can plummet, leading to analysis paralysis.

Devon recounts receiving emails from listeners who feel overwhelmed by the vastness of P&M strategies, prompting her to introduce Chris. Together, they aim to provide a structured framework that helps listeners navigate through these challenging phases without giving up (04:56).

Overcoming the Valley of Despair

Moving beyond initial frustration, Devon outlines strategies to climb the "slope of enlightenment," the phase where increased knowledge and practice begin to restore confidence (10:38). She emphasizes the importance of:

1. Recognizing Progress: Acknowledge that even if confidence dips, "I am actually getting better at this in terms of my knowledge base" (10:38).
2. Incremental Learning: Focus on "one thing at a time," such as optimizing the use of existing credit cards before expanding the portfolio (14:48).
3. Self-Comparison: Measure progress against "where you are coming from" rather than an idealized standard (14:48).

Devon advocates for gradual skill-building, ensuring that each small victory boosts both competence and confidence, thereby moving listeners steadily through the learning curve.

Strategies for Maximizing Points

Devon shares her tactical approaches to accumulating and utilizing points effectively:

• Strategic Use of Existing Cards: Familiarize oneself with current credit cards' reward structures to maximize points without necessarily adding new cards.
• Payment Platforms: Utilize services like Plastique, Melio, or Zill Money to pay expenses traditionally not credit-card-friendly, thereby earning points even with processing fees. For example, Devon highlights how using Plastique with the Chase Business Preferred Card can "earn three times points" on expenses coded as shipping (40:54).
• High-Yield Opportunities: Identify and prioritize expenses that offer significant points returns, such as tax payments or business-related expenditures, ensuring that the points earned outweigh the processing fees.

Devon underscores the importance of math in these decisions, advocating for only pursuing opportunities where the points' value "significantly exceeds the cash cost of the processing fee" (30:15).

Practical Examples and Learning from Mistakes

The discussion includes real-life examples highlighting both successes and missteps in the P&M journey:

• Booking Errors: Devon shares a recent instance where she booked a flight through Alaska Airlines without checking for cheaper options on American Airlines, leading to missed savings (27:18).
• Family Travel: Elaborating on booking award travel for four, Devon provides insights into managing multiple seats and optimizing award availability, especially in premium cabins (43:20).

These anecdotes serve as cautionary tales and learning opportunities, reinforcing the need for meticulous planning and flexibility in strategies.

Advanced Tactics for Families and Groups

When planning award travel for multiple people, Devon offers specialized strategies:

• Flexibility in Travel Plans: Being open to varying dates, airports, and routes increases the likelihood of securing multiple award seats.
• Utilizing Specific Airlines: She recommends airlines like Emirates and Condor Airlines for their reliable business class award availability, essential for group bookings (44:34).
• Transfer Partners: Devon highlights the importance of leveraging transfer partners, such as transferring Amex points to Hawaiian Airlines (in collaboration with Alaska Airlines) to maximize award opportunities (52:19).

These tactics are particularly beneficial for families seeking premium travel experiences without exorbitant point redemptions.

Maximizing Points Through Shopping Portals

Devon discusses the potential of leveraging shopping portals to exponentially increase points:

• Rakuten and Capital One Offers: By timing purchases during peak bonus periods (e.g., Black Friday, Cyber Monday), users can earn up to 20x points (58:29).
• Strategic Purchases: Planning ahead for non-perishable items and bulk buying during high-yield periods can significantly boost points accumulation.
• Stacking Opportunities: Combining shopping portal bonuses with credit card rewards and gift card discounts can further enhance points earnings (63:45).

These methods require planning and discipline but can lead to substantial point gains with minimal extra effort.

Final Tips and Encouragement

Devon wraps up the episode with motivational insights and final tips for listeners:

• Continuous Learning: The P&M landscape is dynamic; staying informed and adaptable is crucial.
• Personalization: Tailor strategies to individual spending habits and goals rather than following one-size-fits-all advice.
• Positive Mindset: Encourage self-compassion and acknowledge that "there is no horrible or bad use of Points" as long as it aligns with personal objectives (66:07).
• Flexibility and Experimentation: Embrace different redemption methods and remain open to adjusting strategies as needed.

Devon emphasizes that mastering Points and Miles is a journey, not a destination, and each step forward contributes to greater travel and financial rewards.

Notable Quotes

• Devon Gimbel: "There’s no one right way to do points or miles. There’s no one right way to earn them or to use them." (02:37)
• Devon Gimbel: "Learn all the potential options out there for you. Is it really, really fun to book a first class flight on JAL through American Airlines for 80,000 points and fly first class from the States to Tokyo and save $20,000?" (66:07)
• Devon Gimbel: "One thing I really like to tell people is no, no, no. Learn all the potential options out there for you." (35:43)

Conclusion

This episode provides a comprehensive roadmap for anyone looking to elevate their Points and Miles game. Devon Gimbel's expertise, combined with Chris Hutchins' insightful hosting, offers listeners actionable strategies to maximize their rewards, overcome common learning obstacles, and ultimately unlock unparalleled travel experiences. Whether you're just starting or seeking to refine your existing strategies, this conversation equips you with the knowledge and confidence to navigate the intricate world of Points and Miles effectively.

For more insights, tips, and detailed strategies on Points and Miles, visit allthehacks.com and explore additional resources linked in the episode's show notes.