Podcast Summary

All the Hacks: Money, Points & Life

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

Host: Chris Hutchins
Date: October 15, 2025

Episode Overview

In this wide-ranging listener Q&A episode, host Chris Hutchins tackles 17 insightful questions spanning health open enrollment, investment strategy, insurance, life and disability policies, gold buying (including the Costco phenomenon), RSUs, AI tools, and more. True to his ethos of “never leaving money on the table,” Chris offers practical frameworks, nuanced personal stories, and concrete tips aimed at helping listeners maximize happiness, get more value, and upgrade their lives efficiently.

Key Discussion Points & Insights

1. Open Enrollment & Health Insurance Decisions

(00:56–29:30)

• Health Plan Choices: Chris describes his family’s journey: from COBRA to Cal COBRA and, ultimately, shopping for independent coverage.

  • He emphasizes the tradeoffs between PPO, EPO, HMO, and High Deductible Health Plans (HDHPs).
  • “If all providers you’re interested in are in an EPO’s network, and it covers virtually everything, you can really cut costs compared to a PPO.” (03:25)

• Why Use High Deductible Plans + HSAs?

  • Triple tax benefit of HSAs (“tax-free in, grow, and out”) is a huge draw.
  • He maxes his HSA each year, saves receipts for future reimbursement, and treats it as a long-term investment bucket.

• Psychology of Paying Out-of-Pocket: Initially feared he’d avoid care, but found that knowing he’d done the math and would save overall made it easier to use the plan (08:05–10:10).

  • “Once we hit our out-of-pocket maximum, it was almost freeing. Suddenly, you realize: this is the year to do all that deferred care.” (09:52)

• Dental, Vision, & FSAs (14:20)

  • Standalone dental/vision often isn’t worth it unless employer-paid (“I found I’d pay more in premiums than I’d get.”)
  • Points to FSA hacks, like maxing out early if you know you’ll leave a job.

• Life, Disability Insurance via Employer (18:21)

  • Always prefer getting term policies independently; employer policies usually don’t transfer if you leave.

• The Difficulty of Independent Coverage: ACA plans in many states offer worse benefits and networks than group/employer plans.

  • “Exchange plans can have terrible networks—like in the Bay Area, some don’t cover Stanford or UCSF at all.” (20:03)
  • Discusses alternatives: forming a business group plan, using PEOs (like Justworks, Trinet), affinity/research partnerships, medical sharing plans (which he’s skeptical of), and direct primary care.

• Pro Tip: Always confirm meds/providers before locking in a plan; some policies have stringent requirements or won’t cover your needs.

2. Investment & Diversification Strategies

(30:45–41:28)

• Staying Invested at Market Highs

  • “Almost every day is an all-time high” historically, so he constantly deploys new savings rather than timing dips (30:55).
  • 90% of his capital is invested, 10% cash (for flexibility/liquidity and in case of a drop).

• Portfolio Breakdown

  • 50% US equities (VTI, direct indexing, etc.)
  • 18% international developed (VEA), 12% emerging (VWO)
  • ~10% split among crypto (mainly BTC), alternatives, and commodity ETFs (which he added years ago and now just holds).

Quote: “That’s 50-18-12... so about 80% is in VTI, VEA, and VWO—the three big index fund buckets. 10% cash, and the rest is alternatives/crypto.” (33:00)

• View on Gold & Precious Metals

  • Chris views gold/silver as speculative: “There’s no intrinsic value, just market sentiment. If you do invest, have a thesis—and crucially, a sell plan. Most people focus on when to buy, not when to sell.” (Gold Q&A at 36:00)

• Buying Gold at Costco

  • A nuanced arbitrage—for the determined, it can be profitable, but success depends on fast-moving prices, tight logistics, and treating it seriously as a business/hobby.

3. RSUs and Stock Compensation

(41:28–43:30)

• Sell Immediately Upon Vesting

  • “You probably already have huge exposure to your company. I always sell RSUs as soon as they vest—you’re already making your employment and maybe your geography correlated.”
  • For private-company stock/RSUs, don’t count on it until you actually have the money in hand.

• Tax Planning: Emphasizes checking with a CPA on RSUs, especially re: tax withholding, exercising illiquid options, and potential for negative surprises.

4. Life Insurance – Avoiding Expensive Permanent Products

(43:30–46:38)

• Fee-Heavy Policies: VUL/whole/permanent life insurance products are almost never the best financial move (“Term + invest the rest always beats bundled products for normal net worths”).
  • If you realize you have a poor-fit product, it’s worth calculating if paying surrender charges now is better than ongoing high fees.

Quote: “Sometimes the best outcome is paying someone to take a timeshare—or a bad insurance policy—off your hands, because the long-term costs otherwise are higher.” (46:27)

5. Navigating Raised Insurance Premiums After an Accident

(48:08–51:53)

• Key Advice: Never drop a household driver from your policy unless they truly won’t drive—liability is too great.
• Shopping around is the best way to offset premium hikes; different insurers weigh accidents/claims differently.
• Raise deductibles to match your true risk threshold.
  • “If you won’t file a claim under $2,000 of damage, a $500 deductible is pointless—raise it and lower your monthly cost.”
• Treat insurance as catastrophic coverage if you have the means.

6. Buying New vs. Used Cars

(51:53–54:41)

• Chris nearly always recommends buying one- or two-year-old certified pre-owned vehicles to avoid the steepest depreciation.
  • Exceptions: niche features only on new, manufacturer incentives (EV credits), or getting only the base features you want.
• New is occasionally justified, but “for value, 1–2 year old CPO is usually best.”

7. Task/Project Management and AI Tools

(54:41–62:00)

• Chris manages tasks on paper—simple, effective, and allows for natural culling.
• Project work goes into Notion or Google Docs.
• AI Tools: Heavy ChatGPT user, uses NotebookLM to process documents/YT videos; highlights the explosion of personal-productivity coding with tools like Replit and Cursor.
  • Creating custom apps is easier and cheaper than ever, even for personal/family use.

Quote: “The long tail of software is now stuff you could totally replace—just go build the tool you need.” (59:20)

• Views AI as key to professional resilience—learn to wield new tools to stay in the top quartile of your field.

8. Stability, Self-Employment, and Buffering Volatile Incomes

(62:00–66:30)

• After leaving stable W2 work, Chris’s income now varies 5x month-to-month—a big adjustment.
• Building extended runway, lowering fixed costs, and embracing frugality have been key.
• “If anything, I wish we took the leap of faith earlier, but I’m glad we saved up first. Planning is everything.” (66:31)

9. Sharing Tips, Deals, and Gift Card Trends

(66:30–73:00)

• Deals, weekly hacks, favorite new recipes, and card bonuses are now shared in a dedicated newsletter section (“My Past Week”)—more real-time and actionable than the podcast.
• Gift card deals (especially for Amazon) aren’t as prevalent as during recent industry “waves,” but Chris promises to flag big opportunities via the newsletter.

Notable Quotes & Memorable Moments

• On Insurance Plan Psychology:
  “I was worried one of our daughters would have a cough and we wouldn’t bring ourselves to go to the doctor... But knowing it was the best financial deal, it didn’t impair me as much as I thought.” (08:05)
• On When to Sell Gold:
  “With speculative assets, you need to have a stance—even stronger than usual. What is the thesis? And importantly: when will I close this position?” (36:50)
• On Buying Used Cars:
  “That first year is the steepest depreciation. I’d buy certified pre-owned unless you need a feature or incentive only available on new.” (54:02)
• On AI and Job Security:
  “If you’re not already experimenting with AI to brainstorm, write, automate, you’re missing out... Learn the tools—combine them with judgment, empathy, strategy, and you’ll be in the top 10%.” (60:19)
• On Frugality and Self-Employment:
  “We’re probably on the frugal side compared to our peer group... our struggle is: when we make more, do we let ourselves spend more?” (65:28)

Timestamps for Major Segments

• Open Enrollment, Health Insurance: 00:56–29:30
• Money, Investing, Diversification: 30:45–41:28
• Gold, Costco, Selling Strategy: 36:00–41:28
• RSUs & Compensation: 41:28–43:30
• Life Insurance Products: 43:30–46:38
• Auto Premiums After Accident: 48:08–51:53
• New vs. Used Car Buying: 51:53–54:41
• Task Management & AI Tools: 54:41–62:00
• Self-Employment & Financial Buffers: 62:00–66:30
• Weekly Hacks & Gift Cards: 66:30–73:00

Recurring Themes and Takeaways

• Always run your own numbers. Never assume more expensive is better—or cheaper—for plans, investments, or insurance.
• Treat insurance as catastrophe protection; don’t overpay for coverage you won’t use.
• Stay in the market and diversify—timing rarely wins in the long term.
• For speculative assets (crypto, gold), have a thesis and specific sell plan.
• Leverage AI as a core tool—adopt early to future-proof your skillset.
• Optimize using the hacks that fit your situation, and cut out what doesn’t add value.

For More Hacks, Deals, and Tips

Subscribe to Chris’s weekly newsletter at allthehacks.com/email for timely deals, bonus ideas, recipes, and more life upgrades not always shared on the podcast.