Jun 13, 2025

You’ve climbed the mountain and now it’s time to come down. In retirement, the question shifts from “Where should I invest?” to “Which account do I take money from first?” It’s not just about risk, but timing, taxes, and long-term flexibility. In this episode, Nick and Jake walk through the three major account types, pre-tax, Roth, and after-tax, and explain how withdrawing from the wrong one at the wrong time could cost you thousands.

They discuss sequence of returns risk, why market losses in early retirement are so dangerous, and how to avoid "catching a falling knife" by planning withdrawals with both market and tax efficiency in mind. If you want your money to last, and your tax bill to potentially shrink, this conversation offers a simple framework for smarter decisions in the withdrawal phase.

Here’s what we discuss in this episode:

💰 Pre-tax, Roth, and after-tax: what’s the difference?

📉 The danger of selling during a downturn

🧾 Why tax timing is just as important as returns

📊 Use each account for what it’s best for

🔒 Building safety nets before the market turns

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