Resources for You

The short answer Only if you were going to buy it anyway. A deduction returns your marginal tax rate, not the full purchase price, so spending money you didn't need to spend still leaves you poorer. Where year-end spending does pay off is timing: pulling a purchase...

The short answer When money you take out of the business as an owner gets recorded as an expense, your profit and loss statement shows the business earning less than it really does. Day to day, nobody notices. But the moment a lender, a buyer or an investor relies on...

The short answer Three federal dates matter to calendar-year service businesses this quarter. October 15 is the final deadline for extended 1040 and calendar-year 1120 returns, and there's no second extension. November 2 is the deadline for your Q3 Form 941 (October...

The short answer:  Getting the most from your bookkeeper comes down to four habits on your side of the relationship. Feed them clean, timely inputs so they're not chasing you for receipts and answers. Set a communication rhythm, a quick weekly touchpoint, a monthly...

Every lower-middle-market deal I have ever seen prices off the same three letters. The seller says the business does two million of EBITDA, the multiple gets applied, and suddenly a number with an enormous amount of judgment baked into it is treated like a fact....

Somewhere in almost every deal I have been part of, someone says a version of the same sentence: the company has audited financials, so we can skip the quality of earnings work. It sounds reasonable. It is also one of the more expensive misunderstandings in...

Here is the answer most firms make you sit through a sales call to get: for a typical lower-middle-market deal, a quality of earnings report costs $10,000 to $20,000 for a focused QoE Lite scope, and $25,000 to $50,000 for a full-scope engagement from a boutique firm....

The short answer:  Probably, yes. Most growing firms accumulate finance tools one subscription at a time until they're paying for overlapping features, seats nobody uses, and apps that solve problems they no longer have. The fix isn't just canceling the obvious dead...

The short answer:  You've outgrown DIY bookkeeping when five things start happening: you're spending more than a few hours a month on the books, you're doing them at night or on weekends, you're postponing decisions because you can't get current numbers, you keep...

The short answer:  The first 90 days with a new bookkeeping provider follow a recognizable arc. Month one brings relief as the backlog clears and someone else owns the books. Month two brings trust, as the numbers start arriving on time and proving accurate. Month...

Before I bought System Six, I had to answer this question with my own money. I was leaving a private equity career to acquire a bookkeeping firm with an SBA loan and a personal guarantee. If AI was about to automate bookkeeping away, I was about to make the worst...

Most explanations of a quality of earnings report are written by firms that sell them, for an audience they assume already knows the vocabulary. I came to this from the other direction. I spent years in private equity reading QoE reports, then spent a year as a...

The business I own today started as one cold email to a stranger. No broker, no listing, no marketplace. In this post I will walk through exactly how that worked: the outreach numbers, the email itself, how the deal almost did not happen, how to tell a real seller...

The short answer: Switching bookkeeping providers takes about 30 days and moves through four weekly stages. Week one is handoff and access: gather your logins, statements, and prior books. Week two is cleanup and migration, where the new provider corrects errors and...

There's a lot of advice about how to buy a business. There's much less about the part nobody can rehearse: the first year of actually owning one. I went through a self-funded search in 2020. In July 2021, I closed on System Six, an outsourced accounting and...

The short answer: To close your books in three days instead of ten, make three changes. Reconcile bank and credit card accounts continuously instead of all at once at month-end. Automate transaction categorization and bill capture so data arrives clean. And run a...

The short answer: Bad bookkeeping rarely shows up as one big bill. It hides in four places: the owner's time spent on financial busywork instead of billable work, the direct cost of errors and compliance penalties, the growth blocked when weak systems force you to...

The short answer: To keep the books clean across multiple LLCs, run each entity as its own complete set of books with an identical chart of accounts, never commingle funds or expenses between them, document every inter-company transaction as it happens, and roll the...

Most guides to outsourced bookkeeping are written by content marketers who have never closed a set of books. Mine is different, because I didn't start in bookkeeping at all. I worked in real estate and then private equity, went to business school, spent a year...

Hannah opened her laptop on a Tuesday morning to find her third tax notice of the year. Different state this time. Same problem. Her payroll provider had missed another filing, and the penalty letter sat there in her inbox like an unpaid bill she didn't owe. She'd...

Caroline thought she'd solved her bookkeeping problem. She runs operations at a 22-person consulting firm in Denver. For the first two years, she handled the books herself, along with everything else. Last spring, she finally hired a part-time bookkeeper — someone...

When Nathan started his strategy consulting firm in 2018, he knew exactly where every dollar went. He had to. With four colleagues in a co-working space and a single QuickBooks login, the financial side of his business fit on one Excel tab. He'd reconcile accounts on...

It's 9:47 on a Thursday night. Rachel, who runs a 22-person consulting firm in the Pacific Northwest, has the kids asleep, a glass of wine poured, and QuickBooks open on her laptop. Again. She's reconciling with June. It's October. Her current bookkeeper is fine,...

You spent weeks vetting your bookkeeping provider. You compared pricing, checked reviews, and asked about software integrations. But here's the question most consulting firm owners never think to ask: who else can see your books? Think about what's actually sitting in...

The invoice arrives on a Tuesday morning, right when you're prepping for a client call. You open it expecting the usual number — the one you've mentally budgeted for — and it's $380 more than last month. No explanation. Just more hours. You pay it, because what else...

It was a Tuesday afternoon when Marcus realized something was wrong. Not catastrophically wrong — just the slow, expensive kind of wrong that's easy to ignore. His office manager, Dana, had spent most of her morning re-entering last week's expenses from a spreadsheet...

Picture this. You're sitting across from a prospective investor. Your consulting firm has a strong team, happy clients, and a growing pipeline. Everything feels right. Then they ask to see your financials. You slide a basic profit-and-loss statement across the table....

Picture this. It's Sunday evening, and you're sitting at your kitchen table surrounded by a small mountain of receipts, printed invoices, and bank statements. You've got a shoebox of expense slips from last quarter that still need sorting. There's a filing cabinet in...

Picture this. It's Monday morning. You sit down with your coffee, open your laptop, and pull up QuickBooks. But something's wrong. The screen doesn't look right. Your data's gone—or worse, locked behind a ransomware message demanding payment in cryptocurrency. Years...