Why Did We Start This?

I use Claude to help me analyze spreadsheets, compare reports, summarize long documents, and ask questions about clean QuickBooks data. But I do not use it as a replacement for bookkeeping judgment. In this Software Saturday episode, Jonathan and I talk about connecting Claude to QuickBooks, why a paid AI plan and careful data settings matter, and how clean books determine whether the answers are useful. I share ways AI can spot trends, inconsistencies, formulas, and industry benchmarks quickly. We also explain where I draw the line: tax advice, unchecked numbers, full reconciliations, and asking AI to clean up...

A business owner finally paid off her COVID debt and built a company that pays her a reliable wage, but she still cannot face another work email. I unpack why profitability is not the same as freedom, why an owner who carries the business day to day may still be thinking like an employee, and why the right assistant should take ownership of email and calendar work instead of creating more oversight. I also share the simple AI inbox system I use to sort messages into categories, the reason I reach out for help when an email feels personal...

A clean balance sheet is not just a nice-looking report. It is evidence that someone has checked what entered and left your business, matched the records to bank and loan statements, and found the mistakes that can cost you money. I use a dry-cleaning jacket to explain why you may not care how the work happens, as long as the result is clean, accurate, and useful. Jonathan and I walk through what a bookkeeper actually does: reconciling accounts, categorizing transactions, watching payroll liabilities, entering bills, catching duplicates, and creating an extra layer of protection against fraud. We also explain...

I put four pieces of popular business advice on trial: hire slow and fire fast, all debt is bad debt, the customer is always right, and you just need to hustle harder. Some of these ideas contain a useful warning, but none should replace sound judgment or a clear view of your numbers. I explain when business debt can support profitable equipment or expansion, why borrowing to cover unexplained operating losses is dangerous, and why more revenue cannot repair broken margins. Jonathan and I also talk about AI in hiring, the cost of keeping the wrong person too long...

A client came to us facing a $171,000 tax bill that did not feel right. As I reviewed the return with our team, we found bookkeeping errors that had inflated the income. One problem was Undeposited Funds: a client payment was recorded there, then the bank deposit was recorded as income again. We also found bank transfers that had been treated as income. Those mistakes can leave an owner paying tax on money that was never additional revenue. We brought the projected liability down to about $114,000, a difference of roughly $57,000. I am sharing this because I want you to ask...

A water damage restoration owner is bringing in about $400,000 a year and still wondering whether the business is worth operating. I break down why the tax bill may not be the real problem, how to separate sales tax from actual business expenses, and why revenue alone tells you almost nothing about the health of a company. Jonathan and I walk through margins, self-employment tax, equipment purchases, possible franchise fees, and the monthly profit and loss trend I would want to see before making a major decision. I also explain why clean books and timely pricing changes matter when supply...

Handing an employee the company card without clear limits is not trust. It is leaving everyone to guess. I am showing you why Ramp has become one of my favorite tools for teams that need better control over spending, travel, receipts, subscriptions, and bill pay. Jonathan and I walk through virtual cards for recurring tools, category restrictions that stop out-of-policy purchases, receipt capture, per diem limits, and approval workflows that put a second set of eyes on bills. I also explain who should use Ramp, why it is better suited to a team with bookkeeping support than a solo...

A young real estate agency owner posted that he has gone almost three years without a day off. He just closed the biggest deal of his career, and the win put him in bed unable to get up, too guilty and too paranoid to take a vacation even though he has enough money to last two years. The question I keep coming back to, and a mentor asked me this years ago, is what is enough. If you already had the revenue you picture in your head, would you still get up and work nine to five? Jonathan and...

Two days ago QuickBooks payroll pulled twenty five thousand dollars out of a business owner's operating account, for payroll taxes she had already paid herself. QuickBooks moved everyone from partial payroll to full this quarter, so they started remitting on her behalf, and she never caught the notice because QuickBooks sends so many emails that we all stop reading them. She called support and was told there was nothing they could do. That money now sits at the IRS as a credit she will burn off over the next two months, and she did not have that kind of...

It is Wednesday, so we spun the wheel and pulled six pieces of advice off the internet to see what survives contact with a real business. Almost none of it did. Sleep when you're dead, which is a lovely idea until you meet me on eight hours. Once you have an LLC your personal assets are protected no matter what, which stops being true the moment you run personal money through the business and hand a court a reason to disregard the LLC you never treated as separate. Never use your own money, just max out business credit cards...

A guy posted on Reddit asking whether it is normal that some months he profits and some months he does not pay himself. We ended up calling him Bob, because Reddit does not hand you a name. Four years in, consistently profitable, right up until he hired an employee to run Facebook ads and an Upwork contractor for email marketing. Now he alternates between profit and loss, skips his own paycheck, and is thinking about getting a job to cover the business. Read that back slowly. He would go get a job so the person he hired to make...

Expensify says it is for solo owners all the way up to enterprises, and that is the part we disagree with most. It is not for solo owners. I used it years ago at the church and it genuinely changed my life, because it was the first app that let me photograph a receipt instead of keeping a spreadsheet and carrying paper around. But it is built for a company with an accounting department or a business manager who can babysit it. It runs on submitted reports, so an employee can spend all month and you see nothing until...

Mindset is a buzzword right now, and I know it makes a lot of Christians nervous. It made me nervous a couple of years ago too, so today I want to rub some cats the wrong way. We grew up being taught that if you open my checkbook you can tell where my heart is. Nobody ever taught us how to think about money, only how to spend it. Then we had dinner with friends this week and one of them apologized for having a guest house, and I told her to stop. I do not care if you...

A couple here in North Texas just got federal prison time for taking $4.2 million from more than forty families across six counties and leaving custom homes unfinished. What got me is that this is the second couple in our area in a few months, and I do not think either of them started out as a con artist. They got in over their head. The line from the court records tells you exactly how it happened: they commingled every client's installment payments in one operating account and used one family's deposit to pay the subcontractors on somebody else's job...

Somebody tells me my CPA is handling my financial strategy, and I nearly always have to say: almost certainly not. Unless you have signed a CFO engagement with them, what you are buying is tax preparation once a year, and if April is the only time you talk to them, it is already too late to do anything strategic. Bookkeeping, CFO strategy, tax preparation and tax planning are four separate services, and paying for one does not get you the others. So ask for a meeting to walk through your return. You know your business well enough to say...

A Bluevine report came out in February that I cannot stop thinking about. They asked 785 small business owners about the reality of running one, and three in four said the trade off was worth it. But 56 percent hit cash flow trouble earlier and harder than they planned for, and only 4 percent regret it at all. So there is a chunk of people who got hit and would still do it again, and those are the gritty ones. Then a woman in one of my Facebook groups posted that she could not make payroll this month, and a thousand people...

We came to you live from the Settled conference on Friday, and I have been sitting with one thing Jason said ever since. Luke says give and it will be given to you, poured into your lap. But you only have a lap when you are sitting down. Standing up there is nowhere for the overflow to go, so every time somebody needs something you are pulling it straight out of your own cup. That is where resentment comes from. I have felt it, resenting the client who asked the fifteenth question this week, and underneath it is fear...

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Today is Software Saturday and we are talking about Bill Spend and Expense, which we joined back when it was Divvy and still use every week. I will say it upfront: we are affiliates. I would also never recommend something I do not use myself. What I really want to get into is the business credit card side of it. Every business needs one, and no, running everything...

Happy Freedom Friday. Penny and Jonathan are recording this one from a coffee shop on the road to the Settled conference in Grapevine, which is exactly the kind of Freedom Friday they built the business for: being able to be at a conference on a Thursday night and a Friday. Nobody set the out of office. The conversation starts with something they picked up the night before, trust God with the results of your life, and Penny turns it into a live question for Jonathan. What if we stopped setting goals like sign twenty new clients this month and...

On Tuesday we told the story of an owner who overpaid the IRS by about forty five thousand dollars because nobody was checking the work. Today is the follow up we promised: the questions to ask before you hand your books to anyone. Penny has roughly fifteen of them, and every one comes from something she has walked into. Will I get reports every single month, and by what date. Can I see the reconciliation reports themselves and not just a summary. Can you explain what these mean in plain English, and how does the profit and loss relate...

It is Wednesday, so the wheel is out and four business sayings go on trial. First one in, last one out gets thrown out fast: presence is not productivity, and Jonathan says plainly he does not want that culture for his team. Fake it till you make it gets rejected too, though not the way you would expect. Penny would rather faith it till she makes it, and she draws a clear line between doing something you have never done before and being dishonest about who you are. Then pricing, where they refuse to give a verdict on purpose...

"I can't afford a bookkeeper." Penny and Jonathan hear it constantly, so today they answer it with receipts instead of opinions. It starts with a client who was running Profit First correctly and then had a tax preparer count every transfer between accounts as income: roughly $90,000 of revenue reported as $280,000. On a conservative estimate, that is about $45,000 overpaid to the IRS, which raises the obvious question of whether you could have hired someone good for $45,000. From there it is one real story after another. $75,000 of overstated income found in the first thirty days. An $11,000 customer check sitting uncashed in...

It is Monday, which means we start before the inbox. Penny opens in Matthew 4, where the first thing the enemy goes after is not Jesus' power but his identity: "if you are the Son of God." Then Colossians 3, and a distinction worth sitting with, that chosen, holy and dearly loved are gifts you receive rather than things you earn. From there it gets practical fast. Penny has been at the homeschool table with a kid in tears over math saying "I'm not good at this," and she hears the grown-up version constantly from business owners: "I am not a...

It's Software Saturday, and Penny is finally saying the thing out loud: QuickBooks was never built for you. Those commercials with the overwhelmed owner who signs up and suddenly has it all handled? That is the pet peeve. QuickBooks is genuinely good software, but it is accounting software made for accountants, and if you have opened it and felt lost, that is the product, not you. Jonathan is the proof, he loves software and it still intimidates him. They get into why QuickBooks Desktop is finished in 2026, why Intuit's AI still misses things any person would catch instantly, and...

It's Freedom Friday, and this one gets uncomfortably honest. Penny and Jonathan share their three wins of the week, and win number one is that they fired their marketing company. Roughly $20,000 spent across agencies in twelve months, about $18,000 with the last one, and exactly one client to show for it. They walk through the math that made the decision for them: a $125 lead that becomes $250 when 80% don't show up, then $375 to $500 once you count the ones who don't even own a business. As Penny puts it, it was a numbers decision, not a feelings decision. Then the good news...

Today's question comes straight from Reddit: a brand-new founder with zero revenue was told by more than one accounting firm to elect S-Corp status right out of the gate — and he wasn't sure why Penny and Jonathan would tell him something different. Turns out an LLC is a legal entity and S-Corp is a tax election, and mixing those two up (plus a little fee-driven upselling from firms that charge more to file an S-Corp return) is exactly how new owners end up locked into payroll they can't actually afford. Penny breaks down why an LLC alone will never pu...

It's Wednesday, which means it's time to spin the Wheel of Absolute Wisdom and put some TikTok "advice" on trial. First up: "your business is your baby" — true, and Penny and Jonathan lean all the way into the parenting comparison (yes, it still cries a lot, no, you don't get to sell it without a plan). Then things get spicy: "open an LLC and run all your personal expenses through it so they become tax-free business expenses" — a hard false, and Penny breaks down exactly why an LLC is a legal entity, not a tax structure, and why the IRS...

Today's Reddit post is a doozy: a 29-year-old COO trying to save his father's $16M logistics company — profitable on paper, but $300K behind on rent and delaying vendor payments just to make payroll. We break down exactly why "profitable on paper" so often doesn't mean money in the bank, what net income actually tells you (and what it doesn't), and the uncomfortable family dynamic at the center of it: a son with all the responsibility and none of the power, while dad still runs personal expenses through the business and refuses to sell assets to save it. Whether or no...

Before we look at a single email, invoice, or spreadsheet this week, we're starting right here — seeking God first. It's Monday Mindset, and today Penny tells the story of a pitch-black morning workout that turned into one of her favorite scriptures: John 1:5 — the light shines in the darkness, and the darkness can never extinguish it. We tie that straight into business: stop being afraid of what you'll find when you turn the light on your finances. Plus, we dig into Gary Keller's The One Thing and figure out the one focus that could make everything else in your business easi...

On Saturday's we review software and today, we’re diving into the magical world of Relay Bank, and trust me, it's like finding a unicorn in a field of donkeys. Seriously, if you’re a small business owner drowning in the chaos of financial systems, Relay is here to rescue you. It’s not just a bank; it’s a game-changer that automates the Profit First method, so you can actually keep your sanity while managing multiple accounts without pulling your hair out. We’re not here to bore accountants—sorry, not sorry—but to help you smooth out your financial...

We've got a gem of a story today, folks, and it’s all about our girl Rosie. She came in hot with a serious bookkeeping mess that had her drowning in confusion and late tax filings, but don’t worry, we saved the day. We'll share how we turned her chaos into clarity and what freedom really looks like in the world of business. Plus, it’s Freedom Friday, so we’re all about celebrating the little wins too! Get ready to hear how Rosie went from stressing over her finances to feeling like a boss, because let’s face it, w...

Caught in the whirlwind of social media fame and financial chaos, YouTuber WhistlinDiesel finds himself at the center of a storm with shocking revelations about tax evasion. Join us as we unpack this sensational story and give our take on the whole mess. If you’re a business owner navigating the murky waters of tax obligations or simply love a good tale of unexpected twists and turns, this episode is for you.

In this engaging episode, we dive deep into the recent arrest of Cody Detweiler, better known as WhistlinDiesel, who is facing serious allegations following his fl...

Ever feel like you’re spinning your wheels in business? We'll that's what we're doing on Wednesday's literally spinning the Wheel of Absolute Wisdom! Join us as we tackle the all-too-common myths that can derail even the most passionate entrepreneurs.

Today, we're diving into the hilariously misguided notion that just building something will magically draw people in. Spoiler alert: it won’t. We’re all about helping those tired business owners ditch the guesswork and finally take control of their finances—because who doesn’t want to reclaim their paycheck and sanity? We’re spinning the Wheel of Absolute...

Today, we’re diving into the wild world of cash flow issues that can make even the most ambitious business owners wanna pull their hair out. We’ve got a real gem of a story from some 25-year-old dude who’s growing his industrial coatings biz faster than he can handle, but guess what? He’s drowning in cash flow problems. Yeah, he’s got clients and jobs lined up, but he’s waiting 30 days to get paid while scrambling to buy materials. Classic case of “I’m rich on paper but broke in real life,” right? We’ll break down what Sam...

Let’s be real, starting a business can feel like a total circus, and that’s exactly what we tackle in this episode. We're diving into the struggles that so many entrepreneurs face—working double time just to keep their heads above water while neglecting their own financial needs. Penny also shares her own story of letting go of control and having some fun!

Every Monday will be Monday Mindset. Before you dive into the endless emails and spreadsheets, it’s time to hit pause and focus on God and your goals. What’s the one thing you can na...