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Deductions Aren’t Missed, They’re Misplaced
Founder, deductions don’t evaporate.
They get lost in:
inboxes
text threads
screenshots
random cards
shared accounts
a Slack message from 6 months ago titled “we need this ASAP.”
This isn’t about knowing tax rules.
It’s about building a system that automatically catches every dollar.
Let’s make that happen.
The 10 Deductions Founders Miss Most
How to Capture Each One Fast
1. Software & Subscriptions
You sign up fast. You forget even faster.
Fix: Use one dedicated business card for all tools. Everything funnels cleanly
2. Contractor & Freelancer Payments
Easy to forget. Easy to deduct.
Fix: Pay everyone through a single platform (Gusto, PayPal, Wise, etc.).
3. Home Office (yes, you probably qualify)
If you work from home, you’re entitled to it.
Fix: Use the Simplified Method, $5 per square foot, done.
4. Phone + Internet
If you use it for work, the expense is deductible.
Fix: Deduct a % of your actual bill; most founders forget this entirely.
5. Equipment + Devices
Laptops, microphones, monitors, and cameras are all deductible.
Fix: Keep a running list in one doc. Add purchases as they happen
6. Education & Training
Courses, books, coaching, certifications.
Fix: Tag all learning-related receipts in a folder, “Learning = Deductible”.
7. Travel (yes, even partial trips)
Flights, hotels, mileage, if work-related.
Fix: Use a mileage app OR track trips on your calendar. Easy.
8. Meals (50%)
Coffee meetings. Founder lunches.
Fix: Add "MEAL" to the memo when you swipe the card.
9. Banking & Processing Fees
Stripe, PayPal, and Shopify are all deductible.
Fix: Pull monthly statements and upload them into your bookkeeping system.
10. Marketing Experiments
That Instagram ad test you forgot about? Deductible.
Fix: Create a “Marketing Tests” category and drop receipts in monthly.
Your New Deduction System
1. One Card, One Channel
Run all business purchases through one card. Instant organization.
2. One Folder to Rule Them All
A single receipts folder (phone or desktop). Everything goes here. No exceptions.
3. Auto-Forward Receipts
Set rules in Gmail: “Receipts,” “Invoice,” “Subscription,” “Payment” → forward to bookkeeping inbox.
4. Monthly 15-Minute Sweep
Categorize expenses
Add missing receipts
Tag deductions
Update your deductions doc
5. Deduction Map
Make a simple list of deductible categories and keep it visible.
This system prevents 90% of missed deductions, without turning you into a tax nerd.
The Savings: $2K–$7K Per Year
Community Note
Founder, we’ve all had that moment where we discover a deductible purchase from six months ago and whisper, “Oh come on…”
Your story will help another founder.
Reply and share:
Your most surprising missed deduction
One system that made capturing easier
The “never again” lesson you learned
We’ll fold your wisdom into the NestLedger Playbook so every founder keeps more of what they earn.
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