Archive - Coffee & Compounding

Three Leaks Quietly Draining Every Business Owner's Exit

The exit isn't the day you sell. It's every decision you made years before that.

Jul 24 • Drew Scott

The Pre-Retirement Tax Strategy That Can Save Six Figures

The gap years before RMDs are the cheapest tax bill you'll ever get to choose.

Jul 22 • Drew Scott

AI & Analog #2: Touching Nostalgia

Secret Wars comics, grandma's house, and the smell that timestamps my whole childhood.

Jul 19 • Drew Scott

1031 Exchange Collectibles: The Myth, Debunked

Why the old real estate trick died for collectibles in 2018, and what still works.

Jul 17 • Drew Scott

How to Build a Paycheck for Life

A month-by-month income map for the 25 to 35 years after your last paycheck.

Jul 15 • Drew Scott

AI & Analog #1: Back from the Future

Toy Story 5, a flip phone, and the timeline that convinced me AI isn't a joke.

Jul 12 • Drew Scott

The Tax Rule That Decides Whether Your Collection Passes Down Tax-Free

The tax mechanic that decides if your kids owe 28% on your collection, or nothing at all.

Jul 10 • Drew Scott

Why the Order You Withdraw Retirement Money In Matters More Than the Amount

The withdrawal order most retirees get backwards between 59 and 67, and the fix.

Jul 8 • Drew Scott

The Retirement Account That Lets You Contribute $270,000 a Year

How a cash balance plan changes the tax math for self-employed earners making $200K+

Jul 3 • Drew Scott

How to Know If Your Fiduciary Financial Advisor Is Actually Working for You

A real case study on what "fiduciary" actually means — and what a real plan looks like.

Jul 1 • Drew Scott

June 2026

Same Card. Same Sale. Two Completely Different Tax Bills.

A pure collector and an active dealer sell the same card for $100,000. Their tax bills look nothing alike. Here's why.

Jun 26 • Drew Scott

Three Tax Traps Waiting in Retirement (And How to Outmaneuver Them)

RMDs, Medicare surcharges, and taxable Social Security. The three-bucket plan to outmaneuver all three.

Jun 24 • Drew Scott

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