Hi, I'm Slava, CEO and co-founder of Jupid. Before starting Jupid, I built Anna Money to $40M+ ARR serving 60,000+ SMEs. Today at Jupid, we're helping American entrepreneurs eliminate financial blind spots through AI-native intelligence.

The $14,457 Chaos

Look at these transactions from our bank statements:

• Southwest Airlines: $676.14 (July 15)

• Southwest Airlines: $676.14 (July 22)

• Sentral San Diego: $942.67 (September 14)

• Best Buy: $352.99 (September 10)

• Walmart: $30.04 (September 11)

• Uber: $19.92 (September 13)

• Klein's Deli: $18.03 (September 14)

• Juke Box Print: $119.83 (August 28)

• Innovative Expo: $414.84 (invoice, October 3)

• Jack Henry Events: $9,200.00 (June 5)

What is this mess? Office supplies? Random travel? Entertainment?

Without context, your bookkeeper would scatter these across a dozen categories. The IRS would see chaos. You'd miss thousands in deductions.

Add One Piece of Context: Everything Changes

"We attended Jack Henry Connect conference in San Diego, September 13-15."

Suddenly:

• Those July Southwest flights? Conference airfare booked early.

• Sentral San Diego? Conference hotel.

• Best Buy and Walmart? Demo equipment and booth supplies.

• Klein's Deli and Uber? Business meals and transport during conference.

• Juke Box Print? Marketing materials for the booth.

• Innovative Expo? Booth design services.

• Jack Henry Events? Conference registration.

Total conference investment: $14,456.90 Potential tax deduction if categorized correctly: $14,364.31 Tax savings at 25% rate: $3,591

But only if you categorize everything properly according to IRS rules.

The IRS Rules That Save (or Cost) You Thousands

Here's what most businesses get wrong and what it actually costs them:

Meals: The 50% Trap

Your receipt: Klein's Deli $18.03 + team dinners $167.15 = $185.18

Wrong categorization: Business expense = $185.18 deduction

Correct categorization: Meals during travel = $92.59 deduction (50% limit)

Cost of mistake: $23.15 in lost tax savings

The 50% limitation on meals returned in 2023 after temporary COVID relief (100% for restaurant meals in 2021-2022 only).

Equipment: Immediate vs. Depreciation

Your purchase: Best Buy demo equipment $1,318.80

Wrong categorization: Office supplies or fixed assets to depreciate

Correct categorization: De minimis safe harbor (under $2,500 per item)

Difference: $264 more in tax savings this year by expensing immediately

Registration: Not Just "Training"

Your expense: Jack Henry Events $9,200

Wrong categorization: Professional development or training

Correct categorization: Trade/business convention expense (IRC §162)

Why it matters: Different documentation requirements and audit triggers

Receipts: What You Actually Need

Per IRS Publication 463, you MUST keep:

• All lodging receipts (any amount) - $1,745.52

• Any expense ≥ $75 - Registration, equipment, booth services

• Expenses under $75 - Receipts recommended but not required

Missing these? The entire deduction could be disallowed in an audit.

The Smart Way: Context-Driven Categorization

Here's how modern AI transforms this chaos into tax savings:

Step 1: Provide Context

Tell your expense system: "We're attending Jack Henry Connect, September 13-15 in San Diego."

Step 2: AI Does the Heavy Lifting

The system:

• Links all San Diego expenses to the conference

• Researches vendors (Innovative Expo → trade show services, not entertainment)

• Applies correct tax treatment automatically

• Flags what needs receipts

Step 3: Ask Natural Questions

Instead of digging through IRS publications, just ask:

"What's our total conference spend?"

$14,456.90 across all categories

"How should these be categorized for taxes?"

• Registration: Convention expense (100% deductible)

• Flights/Hotel: Business travel (100% deductible)

• Meals: Travel meals (50% limitation applies)

• Equipment: De minimis safe harbor (immediate deduction)

• Booth services: Marketing expense (100% deductible)

"What's our actual tax benefit?"

Deductible amount: $14,364.31 At 25% tax rate: $3,591 federal tax savings Note: C-corps save less (21% rate), state taxes may add more

Your Actual Jack Henry Connect Breakdown

Here's exactly how our $14,456.90 breaks down for tax purposes:

ROI Beyond Tax Savings

Tax savings are immediate. But here's the strategic view:

Lead Generation

• 47 qualified leads captured

• Cost per lead: $307.59

• Industry benchmark: $250-500 for quality B2B events

Revenue Impact

• If 10% convert at $5,000 ACV: $23,500 revenue

• ROI: 63% in year one

• To reach 100%+ ROI: Need ~$7,000 ACV at 10% conversion

Hidden Value

• Partner meetings initiated: 8

• Competitive intelligence gathered: Priceless

• Team learning & networking: Unquantifiable

The 30-Second Version

1. Dump all conference expenses into generic "Travel": Lose thousands

2. Properly categorize with context: Save $3,591 in our case

3. Use AI to do it automatically: 30 seconds vs. 6 hours manually

The difference? Proper categorization based on IRS rules, vendor intelligence, and conference context.

Your Conference Expense Checklist

Before You Go

• [ ] Tell your expense tracking system about the conference

• [ ] Use one credit card for all conference expenses

• [ ] Know the current meal deduction rate (50% in 2025)

At the Conference

• [ ] Save ALL lodging receipts

• [ ] Save receipts for anything ≥ $75

• [ ] Note business purpose for unusual expenses

After You Return

• [ ] Separate personal from business expenses

• [ ] Apply 50% limitation to meals

• [ ] Ensure equipment isn't miscategorized as travel

• [ ] Verify all documentation is complete

The Technology That Makes This Simple

This is where Jupid comes in. Our AI:

• Understands conference context from a single sentence

• Researches vendors automatically (Innovative Expo → trade show, not entertainment)

• Applies current IRS rules (updated for 2025)

• Generates audit-ready documentation

No more manual categorization. No more missed deductions. No more IRS anxiety.

Just $4.99/month for your first two months (then $49.99/month). One conference's tax savings pays for 7+ years of Jupid.

Start Trial or Book a Call

Slava Akulov is the CEO and Co-founder of Jupid. Connect on LinkedIn or email slava@jupid.com

Disclaimer: Tax treatment varies by entity type and situation. Consult your tax advisor for specific guidance.

References:

• IRS Publication 463 - Travel, Entertainment, Gift, and Car Expenses

• 26 U.S.C. §162 - Trade or Business Expenses

• IRS Notice 2021-25 - Temporary 100% Deduction for Business Meals (2021-2022 only)

• Treasury Regulation §1.263(a)-1(f) - De Minimis Safe Harbor