Tiller Money occupies a peculiar niche in personal finance software: it's for people who find Mint too limiting and YNAB too prescriptive, but who genuinely enjoy working in spreadsheets. After using it for several months to manage both personal finances and small business expenses, I can confirm it does exactly what it promises—with the critical caveat that calling it 'AI-powered' requires a very generous definition of artificial intelligence.
Tiller Money is excellent at exactly one thing: reliably piping your financial transactions into spreadsheets. If that's your jam and you have the spreadsheet skills to build what you need, it's a solid investment. But don't buy it for the 'AI'—there isn't any—and don't expect it to teach you budgeting or make your financial life easier without significant upfront work on your part.