what.tax

what.tax

Share this post

what.tax
what.tax
Building Wealth From the Ground Up [Part 2]: Forget Busywork — Build Systems That Compound Wealth

Building Wealth From the Ground Up [Part 2]: Forget Busywork — Build Systems That Compound Wealth

Automate every save, outsource every friction point, and reinvest the freed hours into scaling value, not activity.

Max Donovan's avatar
Max Donovan
Jun 29, 2025
∙ Paid
15

Share this post

what.tax
what.tax
Building Wealth From the Ground Up [Part 2]: Forget Busywork — Build Systems That Compound Wealth
12
Share

In Part 1 — “Earn, Save, Invest” — we outlined the 2025 ceilings that enable solopreneurs to shelter six-figure incomes while maintaining growth capital. However, the best tax move is worthless if you forget to execute it in the month you intended. Today, we convert that checklist into a set-and-forget engine.

You’ll see how a single calendar-date transfer can top off an HSA before breakfast, how payroll rules can max a Solo 401(k) automatically, and how an always-on fractional CFO keeps you inside the QBI sweet spot without ever opening a spreadsheet. Stick around to the end, and we’ll show the exact trigger points for rolling founder shares into a $10 million QSBS exit—federal tax-free.


Subscribe to our Premium Newsletter, and the entire resource vault opens up instantly.


Flip the Switch — Your Automatic Cash Pipeline

Start with the stealth tax shelter: the Health Savings Account. On January 2—the first banking day of every year—schedule an ACH for $4,300 if you’re single or $8,550 for family coverage, plus the $1,000 age-55 catch-up. These numbers come straight from Rev. Proc. 2024-25, and they buy you the coveted triple-tax-free combo: deductible on Day 1, tax-free growth forever, and tax-free medical withdrawals later. (irs.gov) By front-loading in the first week, you gain an extra full year of compounding versus the founder who dribbles in money monthly. Pro move: pay current doctor bills out-of-pocket and save the receipts—every unreimbursed slip is a future tax-free reimbursement, effectively turning your HSA into a stealth Roth for healthcare.

Next, weaponize payroll. Tell the processor to siphon $23,500—the complete 2025 employee Solo 401(k) deferral—ratably across 24 paychecks. You’ll never notice the missing cash, yet you’ve locked in the deduction (or Roth space) before Q1 closes. If you’re age 60 – 63, the SECURE 2.0 “super catch-up” lets you bump that figure to $34,750; the rule is optional for employers, so flip the toggle in the admin portal and forget it.

Employer contributions are a different animal because they hinge on final profit. Instead of guessing, build a bookkeeping trigger: when your fiscal year closes, the accounting app measures 20 % of S-corp net, subtracts prior deferrals, and drafts the employer top-off needed to kiss the $70,000 §415(c) ceiling set by Notice 2024-80. The ACH fires in late February—months before the filing deadline—so the money works the market while late filers are still dragging their feet.

This post is for paid subscribers

Already a paid subscriber? Sign in
© 2025 Max Donovan
Privacy ∙ Terms ∙ Collection notice
Start writingGet the app
Substack is the home for great culture

Share