Zero-to-One Concept
I've watched friends panic every April. They stare at TurboTax screens asking "What's Box 12?" and Google frantically, never quite sure if they're doing it right. The anxiety isn't about the tax itself — it's the fear of messing up something important and not knowing until it's too late.
Current tax software hasn't solved this. It just digitized the same confusing forms. You still need to know what to enter and where. If you miss a deduction, too bad — the software won't catch it for you.
This concept explores what tax prep could look like with AI that actually understands your documents, asks follow-up questions like a good accountant would, and explains things in plain English. Not a smarter form — a genuine assistant.
I designed this for three types of people:
Individuals filing a standard W-2 return who often feel intimidated by tax terminology. They want a simple, trustworthy assistant that reduces confusion and increases confidence in the accuracy of their return.
Gig workers, freelancers, and sole proprietors who manage varied income sources, deductions, and expenses. They need automated categorization, real-time deduction suggestions, and help keeping records throughout the year — not just at filing time.
Owners who manage payroll, receipts, business expenses, depreciation, and quarterly payments. They need a centralized, intelligent system that reduces complexity, minimizes mistakes, and helps improve tax outcomes.
TurboTax and H&R Block dominate the market, but they're still just fancy form-fillers. They ask you questions — they don't figure things out for you. There's a gap here for something that feels less like software and more like having a friend who happens to be a CPA.
The goal: make tax season feel like a 20-minute task instead of a weekend-long anxiety spiral.
Most people don't procrastinate on taxes because they're lazy. They procrastinate because the process feels like a trap — one wrong number and you might get audited, or miss out on money you're owed.
Today's tax software expects you to already know the answers. It doesn't help you figure things out — it just asks you to fill in blanks.
What if the software could actually read your W-2, understand what it says, and explain what it means for you?
Primary Users
Secondary Users
What people actually say they want:
The real ask: "I want to feel like someone who knows what they're doing checked my work."
What this does differently:
The goal: finish your taxes feeling like you understood what happened.
Market Size
Revenue Models
Strategic Advantages
Key Assumptions
Risks
Risk mitigation requires human verification flows, clear disclaimers, and grounding AI outputs in verified tax rules.
How we'd know it's working:
User snaps a photo of their W-2. The AI reads it, pulls out the numbers, and says: "Got it — you earned $67,400 at Acme Corp, and they withheld $8,200 in federal taxes. Looking good so far."
No typing. No squinting at Box 12 codes. If something's missing, the AI asks for it specifically: "I don't see state income here — did you work in a state with no income tax, or is there another page?"
Freelancer connects their bank account. The AI scans transactions and starts sorting: "Looks like you spent $340 at Staples and $89 at Best Buy — office supplies? And these 47 Uber rides... were those for work or personal?"
Instead of digging through 12 months of statements in April, everything's already organized. The AI even catches things you forgot: "You paid $1,200 for that online course in March — that's probably deductible as professional development."
User asks: "I bought a laptop for work but sometimes my kids use it. Can I still deduct it?"
AI responds: "Yes, but only the portion used for work. If you use it 70% for business, you can deduct 70% of the cost. Based on the $1,400 you spent at Apple in September, that'd be about $980."
No more Googling "laptop tax deduction reddit" at midnight.
Before you file, the AI does a final check: "I noticed you work from home but didn't claim a home office deduction. Your apartment is 850 sq ft and your desk area is about 100 sq ft — that's a $600 deduction you're leaving on the table. Want to add it?"
It's not just filling in forms. It's actively looking out for you.
Age: 29
Occupation: Customer support representative
Income Type: W-2 employee
Tech Comfort: Moderate
Tax Complexity: Low
Motivations
Pain Points
Needs
"I clicked 'not sure' like five times. That can't be good, right?"
Age: 34
Occupation: Freelancer & rideshare driver
Income Type: 1099s + multiple expense categories
Tech Comfort: High
Tax Complexity: Medium–High
Motivations
Pain Points
Needs
"I have receipts everywhere — my email, my photos, a shoebox. Come tax time, I just guess."
People dread tax season not because taxes are hard, but because the tools make them feel stupid. You upload a W-2 and still have to manually type in every number. You're asked about deductions you've never heard of. One wrong checkbox and you're scared of an audit.
The core problem: tax software treats users like data entry clerks, not people who need help understanding what's happening with their money.
Everyday Filer
As a W-2 employee, I want to upload my forms and have them filled in automatically so I don't make mistakes.
Gig Worker
As a freelancer, I want my expenses categorized automatically so I can maximize deductions without manual sorting.
Small Business Owner
As a business owner, I want clear guidance on what qualifies as a deduction so I can file confidently.
Goal: A W-2 employee finishes their return in under 20 minutes.
Goal: A freelancer stops dreading tax season.
Goal: A small business owner files without needing an accountant.