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

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

Author: Chris Hutchins October 15, 2025 Duration: 1:09:37
All the Hacks: Money, Points & Life
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#250: Chris dives into listener questions, covering open enrollment, investing, buying gold, life and auto insurance, RSUs, practical ways to leverage AI tools and more. Link to Full Show Notes: https://chrishutchins.com/open-enrollment-AMA-2025 Partner Deals Fabric: Affordable term life insurance for you and your family Superhuman: Free month of the fastest and best email with code ALLTHEHACKS Gusto: Free 3-month trial of the #1 payroll software DeleteMe: 20% off removing your personal info from the web Mercury: Help your business grow with simplified finances For all the deals, discounts and promo codes from our partners, go to: chrishutchins.com/deals Resources Mentioned PEOs: TriNet | Justworks Insurance Broker: Rich Sterling Productivity/AI Tools Notion NotebookLM Replit Cursor v0 Figma Perplexity Claude Mesa Homeowners Card (50k bonus with code CHRIS50) $1,200 U.S. Bank Bonus ATH Podcast Newsletter Ep #34: Insider Tricks to Healthcare, Prescriptions and Medical Bills with Marshall Allen Ep 104: Optimizing Your Insurance Policies Ep #140: Navigating Open Enrollment Ep #168: Building an Investment Portfolio to Grow and Protect Your Wealth Ep #248: How to Stop Over-Optimizing and Focus on What Matters with Tim Ferriss Submit questions for our next AMA here Leave a review: Apple Podcasts | Spotify Email for questions, hacks, deals, and feedback: podcast@chrishutchins.com Full Show Notes (00:00) Introduction (00:30) Quick Episode Overview (01:22) How to Select Your Insurance Plan (05:19) Saving with a High Deductible Health Plan (14:19) Tips for Specific Drugs and Providers (15:27) Dental and Vision Plans (17:17) Benefits of FSAs (19:10) Getting Health Insurance Outside of an Employer (21:08) Getting Insurance for Your Business (23:20) Insurance via Medical Research Companies and Affinity Groups (24:52) Direct Primary Care (25:48) Reimbursing Medical Expenses Charged on a Credit Card (30:45) Diversification in an Incredibly High Stock Market (36:20) Investing in Precious Metals: Gold & Silver (40:55) Strategy for Handling RSU Compensation (43:35) Variable Universal Life Policy (48:05) The Rise in Auto Insurance Premiums Following an Accident (55:22) Buying A Used vs. New Car (58:06) Chris's Favorite Work Tools Including AI (01:02:07) Is AI an Actual Threat to Our Jobs? (01:04:26) Chris's Pre and Post W2 Job Experience (01:06:50) Find the Best Deals on the ATH Newsletter (01:10:53) The Next Gift Card Sale 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: 100

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All the Hacks: Money, Points & Life
Podcast Episodes
2025 Holiday Gift Guide and Top Ways to Save This Season [not-audio_url] [/not-audio_url]

Duration: 1:24:30
#255: Here are 100+ holiday gift ideas across tech, kitchen, home, clothing, fitness, kids, and games. I’ll also share tools and tactics to help you find deals and spend less this holiday season. For all the products, li…
The Cost of Always Optimizing with Chris and Amy [not-audio_url] [/not-audio_url]

Duration: 1:12:10
#254: Chris and Amy share a candid look at their life together as two optimizers. They discuss everything from family finances and teaching their kids about money to managing their health, work, and travel. Link to Full…
10 Lessons That Challenged My Thinking on Money and Life [not-audio_url] [/not-audio_url]

Duration: 59:23
#253: My top 10 takeaways from a retreat for high-net-worth investors, which will cover investing, managing risk, investing in your health, building meaningful relationships, parenting with purpose, and defining success…
Family Travel on Points: Tips, Tricks and Tactics with Nick Reyes [not-audio_url] [/not-audio_url]

Duration: 1:25:55
#252: Chris and Nick share strategies to make family travel affordable and stress-free with points and miles. They cover how to find multiple award seats, book business class for families, and their best tips for traveli…
How to Focus on What Matters and Let Go of the Rest with Ryan Holiday [not-audio_url] [/not-audio_url]

Duration: 58:43
#251: Discover why Stoicism matters more than ever and how to make it part of your daily life. We share practical ways to focus on what you can control, build resilience, and cultivate the four Stoic virtues: courage, se…
Earn More Points in Multiplayer Mode with Kai [not-audio_url] [/not-audio_url]

Duration: 50:10
#249: 3x your points and miles with a multiplayer strategy. We break down how to earn, manage, and maximize rewards with a partner, family, or friends. Plus learn how to handle the logistics, emotions, and systems that m…
How to Stop Over-Optimizing and Focus on What Matters with Tim Ferriss [not-audio_url] [/not-audio_url]

Duration: 1:33:48
#248: Learn to escape the trap of over-optimizing and design a more meaningful life. We explore setting boundaries, resetting priorities, and turning failure into fuel for success. We also dive into Tim’s creative proces…
Deep Dive on Bank of America Credit Cards (Up to 5.25% Cash Back) [not-audio_url] [/not-audio_url]

Duration: 1:02:24
#247: Chris dives into Bank of America’s credit card lineup and why he has 5 different BoA cards right now. He'll go over how the Preferred Rewards program can help you earn unlimited 3.3% back on everything. Finally, he…
Contrarian Takes on Money, Risk, and Retirement with Tyler Gardner [not-audio_url] [/not-audio_url]

Duration: 1:11:50
#246: Today we explore contrarian takes on budgeting, the 4% rule, retirement planning, and the risks of blindly investing in bonds. We also cover strategies for investing, spending, and rethinking how to use money with…
How Much Are Points and Miles Worth in 2025? [not-audio_url] [/not-audio_url]

Duration: 1:06:42
#245: Ever wonder what points are really worth? I'll break down the different types of points, how to calculate their value, and the biggest mistakes people make along the way. You’ll also learn when cash back might be t…

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