09/09/2026
Flight #137: Indexing 101 with DFA Rob Harvey
Share your answers below.
You can find show notes, resources and more at: https://tinyurl.com/2ttsnwyn
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09/09/2026
09/07/2026
Flight #137: Indexing 101 with DFA Rob Harvey
Will AI replace your job?
The label on an investment can tell you what it's supposed to do. But does it tell you what you're actually getting?
A fascinating conversation for anyone who wants to understand their portfolio—not just own it.
You can find show notes, resources and more at: https://tinyurl.com/2ttsnwyn
09/03/2026
Flight #137: Indexing 101 with DFA Rob Harvey
Who builds an index?
It isn't necessarily Vanguard. It isn't necessarily BlackRock. And it isn't necessarily the company managing your ETF.
In this episode, Rob Harvey breaks down the often-overlooked relationship between index providers and asset managers—and explains how the rules ultimately shape what investors own.
You can find show notes, resources and more at: https://tinyurl.com/2ttsnwyn
09/02/2026
Southwest Airlines pilots can now designate their Non-Elective Contribution (NEC) as a Roth contribution. However, choosing this option may impact your financial and tax planning.
Unlike traditional Roth contributions, federal taxes are not automatically withheld from these funds at the source. Without careful adjustment, your regular paycheck withholding may fall short, potentially leaving you with an unexpected tax bill or penalties. Review your elections and make sure they fit into your overall financial plan.
Watch the full conversation here: https://youtu.be/M0Sd98LmSzg
09/01/2026
The 401(k) contribution rules have changed this year, and certain settings may warrant another check. The Roth catch-up contribution is not an automatic default, meaning you need to log into your account to make an election. If you previously turned it off to manage cash flow, failing to turn it back on may cause you to miss out on your catch-up contributions.
Be sure to log onto your workplace website to review your contribution percentages to align them with your financial goals.
Watch the full conversation here: https://youtu.be/M0Sd98LmSzg
08/30/2026
Flight #137: Indexing 101 with DFA Rob Harvey
Here's a surprising investing lesson: an index fund's goal isn't to beat its index.
It's to track it as closely as possible.
Rob Harvey joins Pilot Money Guys to explain why that matters, how tracking error works, and what investors should understand before choosing an index fund.
You can find show notes, resources and more at: https://tinyurl.com/2ttsnwyn
08/28/2026
Flight #137: Indexing 101 with DFA Rob Harvey
Think you know what you're getting when you buy an index fund? Think again.
Rob Harvey from Dimensional Fund Advisors joins Pilot Money Guys to unpack the hidden complexity behind indexing—from who creates the rules to why two “small-cap” indexes can perform dramatically differently.
Is your index fund really giving you what you think it is?
You can find show notes, resources and more at: https://tinyurl.com/2ttsnwyn
08/28/2026
For Southwest Airlines pilots considering electing your Non-Elective Contribution (NEC) as Roth, please be aware that federal taxes are not automatically withheld from these funds.
Without proper planning, this choice may result in unexpected taxes due and IRS penalties when tax season arrives. Carefully evaluate your tax plan before making changes to your 401(k) account settings.
Watch the full conversation here: https://youtu.be/M0Sd98LmSzg
08/26/2026
Flight #136: How Much is Enough? with Eric Hubbard
Share your answers below.
You can find show notes, resources and more at: https://tinyurl.com/4fpbawmy
08/24/2026
Flight #136: How Much is Enough? with Eric Hubbard
The FedEx pilot contract brings major financial opportunities — but also important decisions.
We break down pay increases, retro payments, tax considerations, and retirement planning strategies pilots should understand.
You can find show notes, resources and more at: https://tinyurl.com/4fpbawmy
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