Optimizing Vacations, New Ways to Earn Points, Airline Changes and More

Optimizing Vacations, New Ways to Earn Points, Airline Changes and More

Author: Chris Hutchins May 7, 2025 Duration: 1:02:14
#226: From optimizing travel and rewards to new ways to earn points, Chris shares some recent tactics he's picked up on upgrades and award travel. He also covers some flight deals, airline changes, Mother's Day gift ideas, and reflects on recent podcast episodes. Link to Full Show Notes: https://chrishutchins.com/optimizing-vacations-and-new-ways-to-earn-points⁠ Partner Deals Gelt: Skip the waitlist on personalized tax guidance to maximize your wealth Trust & Will: Get 20% off personalized, legally binding estate plans MasterClass: Learn from the world's best with 15% off Vuori: 20% off the most comfortable performance apparel I've ever worn LMNT: Free sample pack of my favorite electrolyte drink mix Bilt Rewards: Earn the most valuable points when you pay rent For all the deals, discounts and promo codes from our partners, go to: chrishutchins.com/deals Resources Mentioned Vacation Homes Pacaso: Free early access and $2,500+ in closing credits here THIRDHOME Exclusive Resorts ATH Hotel Upgrade Program (Password: Perks | Tutorial) Lanai Four Seasons Resort Sensei Maui Montage Kapalua Bay Maui Nui: 20% off with code ALLTHEHACKS Merriman's: Point Menu | Monkeypod Kitchen NordVPN: 4 months free here United’s MileagePlus Program Showing More Awards if You Change This 1 Setting Flight Award Search Tools point.me: 20% off annual plans with code ALLTHEHACKS20 AwardTool: $20 off annual plans with code ALLTHEHACKS Seats.Aero Southwest Assigned Seating Business Payment Platforms Plastiq ← my referral Melio ← my referral Zil Money Last Call: 100k Welcome Bonus Offer Mother’s Day Gift Ideas Ratio Coffee Machines Storyworth: $10 off here Aura Frames: $35 off + free shipping with code ATH Zeel: $25 off here Initial Necklaces: Gorjana Wilder Necklace | Maya Brenner Real ID: Acceptable Identification at the TSA Checkpoint ATH Podcast Ep #224: Airport Lounges: Getting In, Hidden Perks and Expert Tips with Kevin Song Ep #225: Optimize Your Oral Health for a Longer Life with Dr. Mark Burhenne Leave a review: Apple Podcasts | Spotify Email for questions, hacks, deals, and feedback: podcast@allthehacks.com Submit a question for the next AMA here Full Show Notes (00:00) Introduction (02:00) Finding Accommodation in Hawaii (05:37) Overlooked Hotel Upgrade Options (13:05) Strategy to Book Flights to Hawaii: Cash vs. Points (20:44) Chris' Experience Flying Hawaiian Business Class (22:48) The Impact of Having Starlink on Your Flight (25:04) Review of Four Seasons Lanai (29:29) The Experience at Montage Kapalua Bay (34:28) Underrated Hotel Perks (39:58) Why Chris Is a Big Fan of Hawaiian Airlines (42:13) Follow-Up to Lounge Access Episode #224 (43:07) Why You Should Use a VPN to Book Flights (44:29) Flight Award Inventory Trick (45:21) Upgrading Credit Cards for Bonuses and Free Nights (46:51) Weird Emirates Updates (48:10) Big Southwest Changes (52:18) Updates from Bilt (55:03) Leveraging Business Expenses (57:05) Exciting Credit Card Welcome Offers (58:44) Mother's Day Gift Ideas (1:01:27) Reminder: Real ID Deadline (1:02:20) Feedback on Oral Health Episode #225 Connect with Chris Newsletter | Membership | X | Instagram | LinkedIn Editor’s Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. 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. Learn more about your ad choices. Visit megaphone.fm/adchoices

Ever feel like there's a smarter, more efficient way to navigate your finances, your travels, and your daily routines? That's the core question driving All the Hacks: Money, Points & Life. Hosted by Chris Hutchins, this podcast is built on a simple, powerful idea: maximizing value doesn't mean sacrificing enjoyment. Instead, it's about the strategic choices that free up resources-both money and time-for what truly matters. Chris approaches life as a series of systems to be optimized, drawing from his own experience saving millions through meticulous analysis. The conversations here are practical and wide-ranging, moving seamlessly from credit card points strategies and investment philosophies to the less tangible hacks for personal fulfillment. You'll hear from a diverse roster of experts and icons, including Tim Ferriss, Tony Hawk, Codie Sanchez, and Gary Vaynerchuk, who all bring their unique perspectives on building wealth and designing a compelling life. Each episode feels like a focused workshop, offering actionable advice you can use immediately, whether it's planning a luxury vacation for a fraction of the cost or rethinking your approach to career and leisure. This isn't just about frugality; it's about unlocking freedom and excitement through smarter decisions. Tune in for a consistently insightful blend of tactical moves and deeper conversations that challenge the conventional trade-offs between spending, saving, and living well.
Author: Language: English Episodes: 274

All the Hacks: Money, Points & Life
Podcast Episodes
Stop Overthinking and Start Deciding with Derek Sivers [not-audio_url] [/not-audio_url]

Duration: 1:52:11
#273: Learn to stop overthinking and make better decisions. Chris and Derek discuss how optimizing can go wrong, a coin flip trick for making decisions, journaling as a superpower, how your actions might reveal what you…
My Process for Booking Travel with Points & Miles [not-audio_url] [/not-audio_url]

Duration: 54:29
#272: Learn how to turn your points into significantly better travel experiences by following a simple, repeatable system. We cover how to plan, find award availability, choose the right tools, and decide between portals…
How to Actually Live the Life You're Optimizing For with Sahil Bloom [not-audio_url] [/not-audio_url]

Duration: 56:41
#271: Learn why over-optimizing your life can quietly destroy the things you actually care about. Chris and Sahil explore the doorman fallacy, why big life decisions should happen fast, how to use AI as a thinking partne…
Ski Trip Mishaps, AI Interior Design, Reflecting on Life and More [not-audio_url] [/not-audio_url]

Duration: 1:08:15
#270: Chris and Amy discuss lessons from three ski trips with kids, using AI to redesign rooms on a budget, their favorite new gadgets, navigating high-deductible health plans, and more. Link to Full Show Notes: https://…
Credit Cards: What's in My Wallet for 2026 [not-audio_url] [/not-audio_url]

Duration: 1:14:45
#267: Chris reviews his credit card lineup for 2026, sharing which cards he's keeping and canceling and why. He also covers how to evaluate annual fees, the best cards across major spending categories, and the apps he us…
Why Change Is Hard and How to Make It Your Advantage with Maya Shankar [not-audio_url] [/not-audio_url]

Duration: 45:22
#266: Chris and Maya break down the science-backed tools that make change easier and more intentional. They explore why most people misunderstand change, how to anchor your identity to your deeper “why,” and practical to…
I Built an AI Assistant That Works While I Sleep [not-audio_url] [/not-audio_url]

Duration: 51:24
#265: Chris explores how modern AI tools have eliminated the barriers to building software, why planning matters more than coding skill, how anyone can turn a simple problem into a working app faster and cheaper than eve…
Deep Dive on Bilt Rewards and New Bilt 2.0 Cards [not-audio_url] [/not-audio_url]

Duration: 1:15:43
#264: Learn how the Bilt ecosystem works, from earning Bilt Rewards to the new cards, transfer partners, perks, and where the real value is. Whether you’re new or already earning, this is a practical guide to using Bilt…