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
The Simple Path to Wealth and FU Money with JL Collins [not-audio_url] [/not-audio_url]

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#194: Build wealth and achieve financial freedom with three simple, actionable steps. Personal finance expert JL Collins discusses the concept of "FU" money, the importance of living on less than you earn, the power of l…
The Power of Trust and Skepticism with Jamil Zaki [not-audio_url] [/not-audio_url]

Duration: 52:20
#193: Unlock better opportunities, improve your emotional and physical health, and build stronger relationships by embracing “hopeful skepticism.” Dr. Jamil Zaki shares science-backed, actionable strategies to overcome t…
How I Saved Over $20K on a Luxury European Vacation [not-audio_url] [/not-audio_url]

Duration: 1:13:20
#192: Here's how we saved over $20,000 on our recent Europe trip! Learn how to use award flight tools to score affordable business-class tickets, maximize hotel loyalty programs for luxury stays, and find incredible trav…
11 Lessons Every Investor Needs to Know with Ben Carlson [not-audio_url] [/not-audio_url]

Duration: 55:15
#191: Grow your wealth and build a resilient portfolio by making smarter decisions with these 11 investing lessons. Financial advisor Ben Carlson and I share actionable insights on managing risk, overcoming psychological…
Why High-Performers Focus on Energy, Not Time with Sahil Bloom [not-audio_url] [/not-audio_url]

Duration: 48:51
#190: Transform your relationships, productivity, and overall quality of life by discovering how to be intentional with your time. Sahil and I share actionable tactics to build better habits (and get rid of bad ones), im…
My Must-Have Products and Services for Life, Work and More [not-audio_url] [/not-audio_url]

Duration: 59:29
#188: Here are the 130+ things I cannot (or don’t want to) live without, including my favorite tech, web and mobile apps, travel gear, subscriptions, banks and financial tools. I also share health and fitness items, smar…
42 Travel Planning Tips & Hacks from Travel Pro Leigh Rowan [not-audio_url] [/not-audio_url]

Duration: 1:09:15
#187: Learn the art of travel planning to enjoy incredible vacations. Travel pro Leigh and I share over 40 practical tips to create the perfect itinerary, save on flights and hotels, find travel inspiration, experience d…
25 Money Rules (and When to Break Them) with Brian Feroldi [not-audio_url] [/not-audio_url]

Duration: 55:22
#186: We'll break down 25 investing and finance rules of thumb, so you can learn to make better financial decisions, whether your goal is growing your wealth, retiring early, managing your portfolio, buying a car, or man…

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