Guest: Chris Hutchins, host of All the Hacks

Episode theme: Building wealth with meaning—how to design a career (and life) you actually want, while optimizing the money side.

What we cover:

• Meaning > money-first: Chris didn’t start out chasing wealth; he chased options. Early jobs in consulting/banking felt misaligned (little meritocracy, lots of “performance”). That tension pushed him toward work that creates—startups, product, and eventually a podcast.
  
  
• From layoff to leverage: A 2008 layoff forced reinvention. He broke into tech by doing unglamorous, high-initiative work, learning in public, and obsessively networking. Key tactic: create value before you’re hired (he built a full market brief to win a BD role).
  
  
• Career as a cash-flow asset: Once he found work he loved, savings were easier because the job itself provided energy, purpose, and upside. That shift—liking the work—reduced the need to “buy happiness” elsewhere.
  
  
• Optimization without overwhelm: All the Hacks exists to find the 80/20 in money, travel, health, and life. You don’t need to become a points guru or biohacker; borrow Chris’s research and apply the simple levers.
  
  
• Counterintuitive insurance take: When he priced plans, the “best” (premium) plan cost ≈$24k/yr more than the “worst,” while the “worst” plan’s out-of-pocket max was less than that difference. With a real emergency fund and a strong stomach, a high-deductible plan can be rational. (Psychology is the hard part.)
  
  
• Prepay for joy: Pre-buying (subscriptions, passes, prepaid trips) can remove friction and guilt, increasing actual use and happiness.
  
  
• Know your enough: People who don’t know what money is for default to “more.” Define the life you want, price it, then fund that—not a moving target.
  
  
• Audience resonance: “Mini-retirements,” negotiation tactics, and insurance optimization were huge hits; even niche episodes can be life-changing for the right listener.
  
  

Actionable takeaways

1. Design a role you’ll keep doing. Treat your job like part of your portfolio’s fixed-income sleeve: dependable cash flow, lower stress, and compounding skills.
   
   
2. Front-load value. Pitch with a one-pager or mini-audit tailored to the company—proof you’ll do the work.
   
   
3. Run the insurance math (with your EF). Price premiums vs. out-of-pocket max; let your emergency fund shoulder higher deductibles if the numbers favor it.
   
   
4. Prepay strategically. Use prepayment to align behavior with values (fitness classes, transit, annual memberships).
   
   
5. Write money rules. E.g., “Invest 20% before lifestyle,” “Use points for intl. biz class only,” “If it saves 10+ hours/yr, buy it.”
   
   

Lightning-round fun

• Best <$100: Ultrasonic cleaner (for retainers/aligners)—tiny daily upgrade.
  
  
• Most overrated advice: Social-media tax “hacks” that cross legal lines.
  
  
• Apps he likes: A clean net-worth tracker + Copilot for spending (iOS).
  
  
• Guilty pleasure spend: Big annual fees on premium cards—only if the benefits net out.

Find Chris: All the Hacks (weekly deep dives). A great starting point: his “Top 50 Lessons” episode.

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There’s a strange YouTube genre called “What’s in My Bag?” where people pull out chapstick like it’s a state secret. This episode is basically that…except the bag is my financial life. And instead of chapstick, it’s index funds and money markets. Not sexy. Not even the flavored kind. Just the plain, unscented stick you find in your coat pocket three years later — still somehow usable.

So, what’s in my financial bag? Today I’m walking you through my actual accounts: Roth IRA, taxable brokerage, SEP IRA, and yes, the glorified piggy bank that is my money market fund. I’ll explain what’s in each, why it’s there, and how I think about these buckets so you can use the same framework as a mirror for your own setup.

Along the way, I’ll share how I went from aspiring Peter Lynch to preferring mental bandwidth. Why I sometimes hoard cash like a squirrel on Adderall. And why even the smug “just buy the S&P 500 and chill” crowd (myself included) still falls into the trap of trying to outsmart the market — usually by tilting toward “the next big thing” in the most boring way imaginable.

Here’s what we cover:

• Roth IRA: My tax-free sandbox. 100% growth funds. If there’s ever a place to take swings, it’s here.
  
  
• Taxable brokerage: My liquid nest. Efficient, simple, with a healthy pile of cash-like funds as a psychological shock collar reminding me to actually live life.
  
  
• SEP IRA: My tax-bracket tamer. Boring, tax-deferred, locked away for “future Tyler.” (Poor guy.)
  
  
• The irony of tilts: How even with all this simplicity, I still fall into the trap of trying to beat the market with the market.
  
  

The goal isn’t just to get rich. The goal is to make your portfolio so boring you forget it exists — because you’re too busy living the life it was supposed to buy you in the first place.

Hope you all enjoy the show and it offers you something to think about this week!

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This week I’m wading into a swamp I usually avoid like lukewarm gas-station sushi: money and politics. Talking about 401(k) policy across administrations feels like trying to explain cricket at Thanksgiving — half the room politely nods, the other half throws turkey legs.

But here’s the thing: retirement policy matters, no matter who you love or hate in Washington. Whether you get to retire at 65 or keep working until 87 shouldn’t depend on which political team you root for.

In this episode, I walk through how the Obama administration approached retirement savings (think: auto-IRAs, myRA accounts, the Fiduciary Rule) and how Trump’s team countered with their own changes (think: loosening MEPs, alternative assets in 401(k)s, and rolling back fiduciary standards).

We’ll break it down into five big ideas you should care about regardless of politics:

1. Access — Millions of Americans still don’t have a workplace retirement plan. Obama pushed for broader access through auto-IRAs, while Trump’s changes were more incremental. Access matters because participation skyrockets when saving is automatic.
2. Simplicity vs. Shiny Objects — Obama tried to make retirement foolproof with boring products like myRA. Trump went the opposite way, pushing for private equity and alternatives inside 401(k)s. Both miss the middle.
3. Fiduciary Rules — Obama’s Fiduciary Rule aimed to make advisors legally put your interests first. Trump’s team scrapped it. What’s left is a murky marketplace where some advisors are fiduciaries and some aren’t — and most Americans can’t tell the difference.
4. Risk & Alternatives — Alternatives like private equity and real estate can add value — if you know what you’re doing. But without education and guardrails, they’re a chainsaw handed to someone who’s only ever used safety scissors.
5. Education — At the end of the day, policies don’t fix behavior. Education does. Whether you’re handed training wheels (myRA) or a Ducati (alternatives), what matters is whether you know how to use them safely.

My goal here isn’t to stump for anyone. I’m not campaigning (I don’t even like campaigning for Girl Scout cookies). This is about helping you understand how policy shifts could impact your money and your future.

📚 At the end of the episode, I also share a book recommendation that completely changed how I think about investing: Richard Ferri’s All About Asset Allocation. If you’ve ever wanted to understand how to slice up your portfolio without losing your sanity, this is the one.

👉 Listen in to learn how retirement policy really affects your wallet — and how to separate political noise from financial signal.