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Core analyses
Introducing “3-step filing”
A new paradigm for tax prep software
The Freelance Tax Tragedy
How America’s hardest workers lose thousands every year
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Automatic write-off detection
The challenges — and how Keeper is overcoming them
Keeper’s chatbot vs incumbents
A detailed comparison & lessons learned
Document drop-off
Our in-house transformer model, compared to traditional OCR
Ask an AI Accountant: V2
An AI tool fine-tuned on US tax law and fielding user questions
CPA reviews V1 of Keeper’s AI Accountant tool
“I feel like it’s a threat or an opportunity, depending on how you look at it”
Supercharged live assistance, using LLMs
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Culture & news
Trouble on #TaxTok
Viral misinfo encourages gig workers to take bad write-offs
Gig workers favor direct giving
But those donations might not be tax-deductible
Gig workers overpay on their taxes by 21%
Missed deductions include phone bills, software
United States of Side Hustles
The hottest gigs for moonlighters, state by state — and the most lucrative nationwide
The top restaurants for business meals, state by state
From steakhouses to fast-casual favorites
The 1099-K reporting change
Why 30M+ Americans might owe an extra $1,000 in taxes this year
5 tips to level-up your loyalty program
How work platforms use loyalty programs to attract and retain gig workers
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