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How to Turn Your Investment Portfolio Into a Tax-Deferred Retirement Machine
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How to Turn Your Investment Portfolio Into a Tax-Deferred Retirement Machine

A 2025 master class for founders who’d rather grow wealth than bankroll Washington

Max Donovan's avatar
Max Donovan
May 04, 2025
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How to Turn Your Investment Portfolio Into a Tax-Deferred Retirement Machine
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Cold Brew, Deadlines, and the $312K Tax Wire

It’s 6:48 a.m. at a WeWork near South Lake Union. You’re gulping cold brew, sprint-editing a sales deck, when your phone buzzes: “Your IRS payment of $312,417 has posted.”

In that moment, every bootstrapper’s mantra—“reinvest every spare dollar”—collides with the brutal math of taxes, market drawdowns, and a lifespan that might outlast four more iPhone chargers.

If that vibe feels painfully familiar, this playbook is for you. We’ll move from raw cash flow to a lifetime tax-efficient paycheck, using 2025’s fatter contribution ceilings, super-sized catch-ups, and still-alive loopholes before Congress slams the door shut.

Promise: Zero fluff, no spreadsheets required, and each tactic is legal with citations to prove it.


1 The 2025 Reality Check—Why Timing Just Got Urgent

  • Individual tax brackets, the 20 % §199A pass-through deduction, and the doubled estate exemption expire December 31, 2025. (Tax Foundation)

  • New 401(k) employee deferral cap: $23,500; catch-up still $7,500—but ages 60-63 get a one-time turbo catch-up of $11,250 thanks to SECURE 2.0. (IRS)

  • 415(c) combined employer/employee limit rises to $70,000. (missionsq.org)

Translation: You have a 24-month window to shovel profits into shelters that may never be this generous again.


2. Design the “Smile Curve” Cash-Flow Forecast

Retirement spending isn’t flat; it smiles:

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