Ask almost any solopreneur about receipt requirements, and you'll hear some version of this: "You only need receipts for things over $75. Anything under that, you're fine." It gets repeated at office meetings. It gets passed around in Facebook groups. It even gets echoed by well-meaning CPAs who mostly work with W-2 employees. And here's the tricky part: there is a $75 rule in the tax code. The problem is that solopreneurs think it means one thing, but it actually says someth

Most of the startup stories you hear are told looking backward. The product's already built, the wins are neatly stacked, and the founders make it all sound easy. This one isn't that. In Episode 140, I'm not interviewing a guest about their finished company. I'm sitting down with my two co-founders, Laura O'Connor and Eric Hunsberger, while we're right in the thick of launching BKeeperAI. The messy middle. And I wanted to share it while we're still in it. Here's the problem w

Why solopreneurs overpay at tax time and the small shift that fixes it. There's a quiet assumption a lot of solopreneurs carry: that the people who keep more of their money at tax time are simply more organized. More disciplined. Better with spreadsheets. That's not it. The real reason most entrepreneurs overpay isn't laziness, and it isn't math. It's trust. An estimated 40% of small business owners skip deductions they're legally entitled to because they don't trust their ow