The Benefits Gold Mine Playground — The Purposeful Performer

Power View: Your current setup vs. your optimal setup.

Enter what you're doing today. See what's possible. The gap between these two numbers is usually the single cleanest fix in your financial life.

Your Inputs

Your Situation

Annual salary $500,000

Avg annual return 8%

Horizon (years) 30

Marginal tax rate 35%

What You Currently Do

Your 401(k) contribution % 5%

Currently use Mega Backdoor Roth? No

Currently contribute to ESPP % 0%

Currently contribute to HSA? No

Plan Assumptions

Employer 401(k) match (100% up to X%) 4%

ESPP discount 15%

Your current setup

Projected at year 30

Your optimal setup

If you maxed every vehicle

What you're leaving behind

Annual leak: $0/yr

Benefit-by-Benefit Breakdown

Benefit

Current

Optimal

Capture

Your 401(k) Match is free money.

Model 30 years of compounding from just a few years of employer match. Watch the gap between capturing the match and skipping it.

Inputs

Annual salary $500,000

Your contribution (% of salary) 5%

Employer match (100% up to X%) 4%

Years contributing 3

Horizon (years) 30

Avg annual return 8%

Mega Backdoor Roth: Tax-free forever.

Most high earners are phased out of a regular Roth IRA. The mega backdoor routes post-tax dollars into Roth through your 401(k), bypassing the income limits — if your plan allows it.

Inputs

Annual after-tax contribution $30,000

Years contributing 5

Horizon 25

Avg annual return 8%

Your future marginal tax rate 32%

ESPP: A discount you can't replicate.

Your employer lets you buy company stock at a discount, often with a lookback. If you enroll and sell disciplined, the effective return per cycle can be eye-popping.

Inputs

Annual salary $500,000

Contribution (% of paycheck) 10%

Discount 15%

Lookback feature?

Cycles per year 2

Estimated stock drift during cycle 0%

HSA: The triple tax advantage.

Pre-tax in. Tax-free growth. Tax-free qualified withdrawals. No other U.S. account offers all three.

Inputs

Annual contribution $8,000

Years contributing 20

Avg annual return 8%

Your marginal tax rate 35%

RSU Reframe: Would you buy it with cash?

Every share you hold past vest is identical to taking the cash and buying company stock on the open market.

Inputs

RSU vest value $100,000

Combined tax rate (fed + state) 42%

% you choose to hold 100%

Existing employer exposure (% of net worth) 30%

Liquid net worth outside employer $500,000

Cash you'd receive if sold on vest

$58,000

After ordinary income tax

Company stock you're implicitly buying by holding

$58,000

Would you buy this voluntarily?

NQDC: Arbitrage your tax bracket across time.

Defer comp today at a high rate. Pay tax later at a lower rate. See the after-tax difference.

Inputs

Annual deferral $100,000

Years deferring 5

Years until payout 15

Current marginal tax rate 45%

Future marginal tax rate 28%

Avg annual growth rate 6%

Ask the AI Twin.

Stuck on a term from the lesson? Ask me. I'll answer in Brandon's voice on anything specific to this lesson. For deeper follow-ups, I'll hand you off to Claude.

Brandon's AI Twin

I answer questions about Lesson 4 only. Corporate benefits, 401(k) match, Mega Backdoor Roth, ESPP, HSA, RSUs, NQDC — the mechanics, the tradeoffs, and how I think about them.

I'm built on Claude. Every question you ask can also be routed to Claude directly for a deeper conversation.

Scope note: This Twin is trained on the content of Your Corporate Benefits Are an Untapped Gold Mine. If you ask something outside the lesson, I'll point you to the right place.

AI TWIN

Hey — welcome. Try one of the suggested questions below, or ask your own about Lesson 4.

Want to go deeper? Any question can open in a full Claude conversation. Free to start, sign-in required.

A quick note: This tool is educational, not financial advice. It simplifies real tax rules and plan mechanics for illustration. Consult a qualified CPA or financial advisor before making decisions about your own benefits. No guarantees. It's your money, so it has to be your decision in the end.