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

All the Hacks: Money, Points & Life

Chris Hutchins

Business, Education, Investing, Society & Culture, Places & Travel, Self-improvement

4.7 • 1.4K Ratings

🗓️ 15 October 2025

⏱️ 74 minutes

🔗️ Recording | iTunes | RSS

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Summary

#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: [email protected] 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

Transcript

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0:00.0	If you're interested in building an investment portfolio, making the right choices during open
0:04.4	enrollment or AI tools, then you'll love this episode because I'm tackling 17 different great
0:09.8	listener questions you all sent in, which also includes topics like buying gold, managing
0:14.6	RSUs, life insurance, dealing with insurance premiums after an accident. There are timestamps
0:19.9	in the show notes, so if you want to find something specific or come back to it later, you can absolutely do that.
0:25.4	And if you want to keep upgrading your money points in life, click follow or subscribe.
0:30.7	Okay, before I jump in, first off, thank you so much to everyone who sent in all the questions
0:35.7	I'm going to cover today. There were way more
0:38.0	than we'll get to in this episode, so I divided them up into a few different categories. And I'm
0:42.7	going to try to tackle them regularly in episodes like this. So if you have other questions,
0:47.1	please keep them coming. You can submit questions to us by going to all the hacks.com slash
0:52.1	AMA. And that way they're ready for us when we prep the next episode.
0:56.5	So the first question I want to tackle is very relevant to this time of year. And that is how I'm
1:01.4	thinking about open enrollment, especially when it comes to health insurance. So first off,
1:06.0	if you go back to episode 140, which was a couple years ago, I did a really deep dive on open enrollment and a lot of
1:12.3	my thoughts. So today, I'll kind of cover a high level version of that and some of the things that have
1:17.2	changed. But if you want to go even deeper, I definitely recommend going to give that episode a listen.
1:22.5	So first off, my personal situation is that when my wife left her job at Wealthfront, we went on Cobra.
1:29.0	So we have insurance through Wealthfront. After 18 months, Cobra runs out. Fortunately, in
1:33.6	California, there's a program called CalCobra that can extend that for another 18 months. But at the
1:38.8	end of those 36 months, you've got to figure it out on your own. And so we are coming up on that
1:44.0	moment of having to do that.
	...

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