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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 we set out to solve. If you're a solopreneur, a real estate agent, a contractor, or a one-person shop, you know exactly how tax season goes. Receipts everywhere. Expenses you can't quite remember. A long weekend lost to sorting a shoebox so your CPA can make sense of it. As Laura put it, the finance side of business is the part most people grit their teeth through, and it's also what keeps the whole thing running. So we asked a simple question: what's the easiest way people already stay in touch about the things that matter? You don't open an app to plan dinner with a friend. You text. So BKeeperAI lives where you already are. You snap a photo of a receipt, text it, and you're done. No app to download, no software to learn, no password to forget. But the part I'm proudest of is the part that's harder to scale, and that's exactly why we kept it - the human verification. When Laura first walked Eric and me through an exercise to find what each of us cared about most, we landed in three different places. For Eric, our CTO, it was accuracy. For me, it was ease. For Laura, it was the human. And when we asked ourselves the hard question, if everything else fell away and we could only get one thing right, we agreed it had to be the human support. Because we've all lived the other version: locked out of a platform, no one to call, hours lost to a chatbot that can't actually help. We didn't want to be one more source of that frustration. While AI is core to how the product works and how Eric built it. Behind it, there's a real person making sure your expenses look right. We even joked in our brand manifesto that we're not a SaaS company at all. We're an Accountability-as-a-Service company. A few other things we get into: The decision we debated far longer than you'd guess (it wasn't the tech, it was tone). Why "tension" and "conflict" are not the same thing, and why I now want a founding team that has plenty of the first kind. What each of us would tell ourselves three months ago. If you've ever thought about building something of your own, or you just want tax season to stop being the worst week of your year, I think you'll get a lot out of this one. Follow Laura. Follow Eric. Follow Christine. Originally published on Post & Beam Creative on 6/11/26.

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 own records enough to claim them. The receipt is long gone. The note was never written. And when you can't prove it, the safest-feeling move is to leave it off. So you pay tax on money you already earned and already spent on your business. Every year. What does that actually cost you? Estimates put the cost of inconsistent expense tracking at $4,000 to $10,000 a year in missed deductions for the average entrepreneur. Mileage alone is a big one: at the 2026 At the standard rate of 72.5 cents per mile, missing just 3,000 business miles leaves more than $2,000 on the table. This is not theoretical money. It's yours. You drove those miles. You took that client to coffee. The only thing standing between you and the deduction is a record you can stand behind. The deductions solopreneurs miss most The pattern is almost always the small, in-the-moment expenses, the ones too minor to feel worth saving, that quietly add up to thousands: The drive between showings. Parking at an open house. The toll on the way to the title company. Your vehicle registration and a business-use slice of your car wash and roadside assistance. Your home office and everything attached to it. If you have a space used regularly and exclusively for business, a percentage of your rent or mortgage interest, utilities, internet, insurance, and HOA fees may be deducted from it. The software you already pay for. Your CRM, e-signature tool, cloud storage, design subscriptions, and scheduling tools. If you use it to run your business, it's almost certainly deductible. Client meals. Coffee with a client, lunch with a referral partner, food at a presentation, all 50% deductible when there's a real business purpose, and you note who was there and why. (Entertainment like game tickets and concerts is not, so don't bother claiming those.) Cash, the easiest to lose. Parking meters, tips for the bellhop at a conference, and a $6 toll. Legitimate every time. Forgotten almost every time. The myth that's quietly costing you money You've probably heard that you "don't need receipts for anything under $75." Half-true and the half that's wrong is expensive. Here's what the rule actually says. For certain categories like travel, meals, gifts, and listed property like your vehicle, the IRS doesn't require you to keep a paper receipt for individual expenses under $75. (Lodging is the exception: a hotel always needs a receipt, no matter the amount.) But waiving the receipt does not waive the record. For every deduction you claim, five dollars or five thousand, you're still required to be able to show four things: The amount The date The vendor or payee The business purpose For meals and travel, add a fifth: who was there and why. So the "under $75" rule isn't permission to forget the expense. It's permission to skip one piece of paper as long as you've captured everything else. The solopreneurs who get this wrong don't get audited for claiming too much. They quietly under-claim because a deduction with no record to back it feels too risky to take. The fix is simple, and it's the whole point: capture a record of everything, in the moment. The shift that actually works Here's the part nobody tells you: the answer isn't more discipline. You don't need to become a different, more organized person. You need a system that fits the life you already have, one that captures the record when the expense happens, not at 11 p.m. in April when you're staring at a shoebox. That's what we built BKeeper to do. Snap. Text. Done. You text a photo of the receipt. Our AI reads it and captures the category, date, amount, and context. Then a real person on our team verifies it. We're AI-Powered, Human-Verified, and it's the reason you can actually trust what comes out. No app to open. No new login. No software to learn. The result isn't just an organized folder. Its records are clean enough that you'll actually claim every dollar you earned and hand your CPA something they can use, instead of apologizing for it. Stop losing deductions you've already earned. See how BKeeper works. This article is for informational and educational purposes only and is not tax advice. Tax laws change frequently, and individual circumstances vary. Always consult a licensed tax professional before making tax decisions. Sources 2026 IRS standard mileage rate (72.5¢/mile) — Internal Revenue Service, IR-2025-128 / Notice 2026-10. The "$2,000+ on 3,000 miles" figure is the rate applied to 3,000 miles (3,000 × $0.725 = $2,175). $4,000–$10,000/year in missed deductions — Bench Accounting and the National Small Business Association. (Confirm before publishing — see note.) 40% of small business owners avoid deductions they're entitled to because they don't trust their records — QuickBooks. (Confirm before publishing — see note.) Business meals 50% deductible; entertainment non-deductible — IRS Publication 463; Tax Cuts and Jobs Act of 2017. The $75 receipt threshold, the four substantiation elements, and the lodging exception — IRS Publication 463; Treasury Regulation § 1.274-5(c)(2)(iii); Internal Revenue Code § 274(d).