The Investor’s Tax Calendar and the Critical Deadlines You Shouldn’t Miss
Capital-gains timing, quarterly tax checkpoints, and the 2025 contribution cut-offs that separate tax-efficient founders from penalty payers
⚡️ 2025: The Year the IRS Charges Interest Like a Credit Card—and How You Can Make It Pay You Instead
Entrepreneurs forked over $7 billion in penalties last tax year—4× 2022—and the carnage hit founders who missed a deadline. Stack that with a 7 % underpayment rate for the first half of 2025, and every late voucher snowballs against you faster than a VC down-round.
Yet inflation tweaks have quietly widened your escape lanes:
Standard deduction jumps to $15k single / $30k joint.
The 0 % long-term gains band stretches to $48,350 single / $96,700 joint—and the 20 % cliff now hides beyond $533k.
Contribution ceilings rise: deferral limit $23,500 on your 401(k), IRAs hold at $7k, HSAs pop to $4,300 / $8,550.
Here’s the kicker: Most founders will still overpay because they don’t know when to move.
In today’s Premium playbook, you’ll get the exact calendar I use with seven-figure clients:
A month-by-month cash-flow map that keeps the IRS off your back—and your money compounding.
Swipe-file checklists for PTET elections, QSBS trust stacking, and crypto wash-sale pivots.
The automation workflow (Zapier + Plaid + Slack) that slams a warning on your phone before a penalty meter starts.
Upgrade now—and make 2025 the year the tax code pays you for perfect timing.
1. Play the Brackets—Capital-Gains Harvesting
Why it matters: The jump from 15 % to 20 % on a $1 million gain is a $50,000 check to Uncle Sam. Hit the 0% bracket, and that check becomes $0.
2025 thresholds at a glance (single filers):
0 %: $0 – $48,350
15 %: $48,351 – $533,400
20 %: $533,401 + (NerdWallet)
Founder scenario: A solo SaaS owner projects $ 200,000 AGI. On December 20, she prepares $30,000 in 2026 marketing costs, reducing projected AGI to $170,000. That lets her realise $40,000 of Apple stock gains inside the 0% bracket—federal tax: $0. State tax, if any, still applies.
NIIT trip-wire: Modified AGI over $200 k single / $250 k MFJ pulls in the additional 3.8 % Net Investment Income Tax. (IRS) Offset with passive real-estate losses or push the sale into January 2026 if next year’s income will be lower.