5 Things I Will Never Spend Money On as a Multimillionaire (And 5 That Are Worth Every Penny)

Sep 28, 2026

What’s truly worth paying for when you have money to spare? This conversation explores generosity, capsule wardrobes, books, house cleaning, car leasing, and long-haul travel upgrades. It also questions short-haul first class, expensive wine, status-driven luxury, and outsourcing enjoyable chores. The central theme: spend on time, health, peace, and connection, not appearances.

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ADVICE

Use Small Tips To Create Real Generosity

Tip 30% for genuinely excellent sit-down service when the extra amount is financially insignificant.
Tyler frames generosity as a purchase that improves both the recipient’s circumstances and the giver’s happiness.

ADVICE

Build A Capsule Wardrobe Once

Build a capsule wardrobe around a few high-quality staples to eliminate recurring clothing decisions.
Tyler wears dark jeans, solid shirts, white T-shirts, and one good jacket, buying multiples of proven favorites.

INSIGHT

Books Deliver An Extraordinary Return

Books offer unusually high returns through sustained cognitive engagement, learning, and rereading.
A Yale study found book readers over 50 had nearly a two-year survival advantage over non-readers.

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And as always, a MASSIVE thank you to this week's sponsors:

Momentous⁠ → ⁠⁠livemomentous.com⁠ Use code Tyler for up to 35% off your first order!

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And on to the show notes!!

Most people spend decades learning how to make and save money.

Far fewer learn how to spend it well.

In this episode, Tyler shares two very personal lists: five things he’ll happily overpay for, and five things he refuses to spend money on again.

Not because one list is objectively right.

Because the point is figuring out your own list.

In this episode, Tyler covers:

Why many well-funded retirees still struggle to give themselves permission to spend
Five things Tyler believes are genuinely worth the money, from generous tipping to buying back time
Why a capsule wardrobe, books, house cleaning, and even leasing a car can make sense when they solve the right problem
Five purchases he’s done with—including short-haul first class, expensive wine, and other versions of “luxury” that don’t actually improve his life
Why outsourcing tasks you hate can increase happiness—but outsourcing things you enjoy can do the opposite
How to separate spending that buys time, health, peace, or connection from spending that mostly buys an audience
The exercise of building your own “worth it” and “never again” lists

The core idea:

The money was never the finish line. It’s a tool for buying more of what you already value.

Spend generously where it meaningfully improves your life.

And stop paying for things you only thought you were supposed to want.

If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps.

Hope this gives you something to think about this week.