Point Me To First Class
Devon Gimbel MD
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 earn credit card points for travel.
Turn credit card points into travel.
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 earn credit card points for travel.
Turn credit card points into travel.
Episodes
Mentioned books
Mar 30, 2026 • 1h 6min
161. Points Earning Unicorns: Risk vs. Reward for Outsized Deals with Dr. Sujatha Murali
Dr. Sujatha Murali, an oncologist who studies decision-making, joins to dissect rare, outsized points deals. They unpack the psychology that makes multipliers irresistible. Short-tests, reading terms, and practical checklists get covered. Real cases like Simply Miles and Kate Spade illustrate risk versus reward.
47 snips
Mar 23, 2026 • 55min
160. The Uncapped Value of Hilton Free Night Certificates with Jess Field
Jess Field, points-and-miles educator and founder of Points Talk Squad, explains Hilton free night certificates and their uncapped value. She discusses how to earn certificates via Amex cards, combining them with points for longer stays, and top aspirational properties like Conrad Bora Bora. Practical booking tips, timing and expiry strategies, and when to target multiple certificates round out the conversation.
16 snips
Mar 16, 2026 • 1h 43min
159. The Hyatt Award Chart Overhaul: Points Strategy Shifts with The Points and Miles Doc
Kelly, the Points and Miles Doc — a concise points and hotel strategy analyst — breaks down Hyatt's major award-chart overhaul. They walk through the new multi-tier pricing, who stands to lose most, and why Hyatt made the change now. Short, practical talk on booking urgency, certificate usefulness, elite access, and which high-end stays to consider before pricing shifts.
42 snips
Mar 9, 2026 • 30min
158. Before You Pay Your Taxes by Credit Card: Avoid These Points-Killing Mistakes
Planning tax payments early to avoid last-minute failures. Choosing which cards and timing new applications to maximize points. Navigating federal payment platforms, per-processor limits, and splitting large bills. Using PayPal smartly while avoiding wrong-account charges. Amex-specific tips for virtual numbers, spend bonuses, and meeting thresholds for bonus earning.
64 snips
Mar 2, 2026 • 43min
157. Shifting My Strategy: Why I'm Pursuing Status in Multiple Programs This Year
The host explains why they are chasing top-tier status in multiple loyalty programs this year. They list four specific statuses being pursued and detail the concrete perks that matter for family travel. The plan covers how each status will be earned and why some card benefits can substitute for status. Four key questions to ask before pursuing any status round out the strategy discussion.
15 snips
Feb 23, 2026 • 37min
156. Making Large Family Award Travel Actually Work with Dr. Alison Curfman (Part 2)
Dr. Alison Curfman, a physician-entrepreneur and frequent family traveler, shares systems for managing travel with many children. She covers getting kids to sleep on overnight flights, stretching hotel breakfasts and snack kits, low-stress evening routines, morning family meetings to reduce meltdowns, giving kids planning and navigation roles, and using AI to create itineraries and learning activities.
22 snips
Feb 16, 2026 • 48min
155. Planning Award Travel for Large Families with Dr. Alison Curfman (Part 1)
Dr. Alison Curfman, a pediatric emergency physician and entrepreneur who travels internationally with a large family. She explains anchoring trips on long-haul award availability and building flexible itineraries around seats. Learn about positioning flights as part of the journey, Hyatt-focused hotel strategies, packing light with kids, and using spreadsheets to track complex group bookings.
33 snips
Feb 9, 2026 • 30min
154. The Most Memorable Credit Card Points Lessons from Real Travelers
Community-sourced travel points lessons highlight transfer timing surprises and phantom award space. Practical tips cover account setup, alerts, and shopping portals to boost earnings. Creative tactics include one-ways, repositioning, and flexibility to unlock value. Advice stresses booking now, automating credits, saving points for top transfer partners, and actually spending rewards instead of hoarding.
22 snips
Feb 2, 2026 • 31min
153. Avios Explained: Understanding Transfers & Maximizing Award Flights
They break down what Avios are and which airlines share this points currency. You hear how Avios can move between partner accounts and why that creates unique booking opportunities. The conversation covers transfer tricks, Points Boost buying options, and award pricing arbitrage across programs. Practical setup tips, common transfer sources, and warnings about fees and refund rules are also highlighted.
28 snips
Jan 26, 2026 • 49min
152. Building Wealth Beyond Travel: Financial Planning for High-Earners with Lauren Oschman
Lauren Oschman, founder of Vestia Personal Wealth Advisors who helps physician families with holistic wealth planning. She discusses aligning money with personal values, the full scope of planning beyond investments, tax and estate strategies, contract negotiation, and tailored approaches for dual-earner households and women building financial confidence.
