All the Hacks: Money, Points & Life

Chris Hutchins
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52 snips
Dec 17, 2025 • 55min

My Top 5 Mistakes with Points & Miles

Dive into the world of points and miles with insights on the biggest downfalls in maximizing value. Discover the hidden costs of status and why chasing elite tiers might not be worth it. Learn about opportunity costs and how overvaluing points can lead to losses. Chris shares why hoarding points can be detrimental and offers a practical plan for cashing them out effectively. With real-world examples, he challenges common assumptions and emphasizes valuing your time in this journey.
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390 snips
Dec 10, 2025 • 1h 13min

End of Year Checklist for Your Taxes, Points and Miles

As the year ends, crucial tax strategies are unveiled to maximize your deductions. Discover the benefits of donating appreciated assets and how bunching contributions can hedge against future limits. Learn about new deductions for car interest and seniors, alongside the mechanics of the mega backdoor Roth. For the travel-savvy, tactics for securing elite status and unmissable credit card perks come to light. Additionally, get insights on 529 plans and the new child investment accounts launching soon.
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293 snips
Dec 3, 2025 • 59min

The Easy Way to Build and Maintain Meaningful Relationships with Nick Gray

Nick Gray, an entrepreneur and author known for founding Museum Hack, shares his expertise on building meaningful relationships. He emphasizes the importance of giving more than receiving in friendships and reveals effective tactics like hosting meetups and sending friends newsletters. Nick also simplifies hosting with his Two-Hour Cocktail Party formula and discusses the benefits of creating a personal website. Plus, he shares insights on budget-friendly cruises and the value of regular events to maintain connections.
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260 snips
Nov 19, 2025 • 1h 25min

2025 Holiday Gift Guide and Top Ways to Save This Season

Explore over 100 unique holiday gift ideas ranging from tech gadgets like 3D printers to cozy home comforts like Purple pillows. Discover innovative kitchen tools, including the Ninja Creamy for healthier desserts and the versatile Thermomix. Learn about cost-saving strategies using tools like Keepa and Cashback Monitor to score the best deals. Uncover thoughtful gift options for kids and adults alike, from skateboards to MasterClass memberships, and find out how to layer discounts for maximum savings!
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252 snips
Nov 12, 2025 • 1h 12min

The Cost of Always Optimizing with Chris and Amy

Chris and Amy candidly discuss the complexities of life as optimizers, from tackling a furniture purchase that spiraled into conflict to efficient reselling techniques. They share innovative ways to teach their kids about money, including hands-on activities and college savings strategies. The couple debates the balance of technology exposure for children and explores the values of free-range parenting. Additionally, they reflect on health advocacy, transitioning childcare, and proactive strategies for aging parents, all while contemplating a mini-retirement.
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738 snips
Nov 5, 2025 • 59min

10 Lessons That Challenged My Thinking on Money and Life

Tad Fallows, co-founder of Long Angle and former iLab Solutions co-founder, shares insights from a retreat for high-net-worth investors. He emphasizes that health is the most vital asset, advocating for personal health advocacy and smart fitness investments like trainers. The conversation also explores building meaningful relationships through intentional interactions and travel. Tad discusses the importance of 'lighthouse parenting,' allowing kids to face challenges, and highlights the need to align financial strategies with true life goals rather than tax optimization.
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223 snips
Oct 29, 2025 • 1h 26min

Family Travel on Points: Tips, Tricks and Tactics with Nick Reyes

Nick Reyes, a seasoned traveler and writer for Frequent Miler, shares expert insights on making family travel a breeze using points and miles. He discusses strategies for booking business class for families, finding multiple award seats, and managing jet lag with kids. Nick also offers tips on choosing family-friendly accommodations, the perks of kids in premium cabins, and essential gear for travel. Plus, learn how cruises can simplify family trips and discover top destinations for family adventures around the world.
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364 snips
Oct 22, 2025 • 59min

How to Focus on What Matters and Let Go of the Rest with Ryan Holiday

Ryan Holiday, a bestselling author and modern Stoic thinker, shares insights on the practical application of Stoicism for today’s chaotic world. He emphasizes focusing on what you can control and outlines how to cultivate the four Stoic virtues: courage, self-discipline, justice, and wisdom. Ryan discusses the importance of re-evaluating first impressions, the futility of complaining, and practices to foster a Stoic mindset, like journaling and pausing before reacting. His perspective offers a roadmap for thriving amid uncertainty and finding true happiness.
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393 snips
Oct 15, 2025 • 1h 10min

Open Enrollment, Diversifying Investments, Buying Gold and More Listener Q&A

Listeners dive into important topics like navigating open enrollment, exploring health insurance plan options, and maximizing FSA benefits. Chris discusses investment strategies, including diversification amidst a high stock market and insights on buying gold. He warns about the complexities of variable universal life insurance, shares tips on handling RSU compensation, and emphasizes the benefits of AI tools in enhancing productivity. The discussion offers practical advice for both personal finance and transitioning to self-employment.
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182 snips
Oct 8, 2025 • 50min

Earn More Points in Multiplayer Mode with Kai

Discover how to triple your points and miles by teaming up with a partner or friends. Learn the ins and outs of managing multiple accounts and maximizing referrals. Kai shares his strategy for handling the logistics and emotions that come with churning. Explore the benefits of teaching family members about building credit and travel dynamics, plus tips for streamlining the process. From overcoming stress in booking to leveraging shared resources, this discussion is packed with actionable insights for avid points enthusiasts.

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