Why Did We Start This?

We Tested 7 Pieces of Viral Business Advice | Wheel of Wisdom

Can an owner take a vacation in the first three years? Is gas for your everyday car a business write-off? Does a new business idea have to be something nobody has tried?

Strong Sales, Low Profits, and an Alleged $1.3 Million Embezzlement | Real Finance Struggles

I keep hearing from owners who see strong sales but cannot understand why the profit is missing. In this episode, Jonathan and I unpack a Chicago case in which prosecutor

$300,000 Bakery Investment, $40,000 Owner Pay | Monday Mindset

A San Francisco baklava bakery has a seven-person team, a handmade product, and an owner who says he took home around $40,000 last year after investing about $300,000 to

Why Spreadsheets Fail Your Business | Software Saturday

I love a good spreadsheet for a quick calculation, but I hate relying on one to run the financial side of a business. In this Software Saturday episode, Jonathan and I lo

$40,000 Tax Bill, No Reserve: Start Before It Is Due | Friday Fundamentals

Tax money can disappear before you ever see the bill when it sits beside payroll, software, and everyday spending. I have seen owners reach tax time facing a $40,000 bill

Why $10,000 in Bookkeeping Can Save You More

A million-dollar business with five employees was still relying on the owner to keep up with the bookkeeping, and the delay ended in tax penalties. I have seen this patte

Spend, Give, Grow, or Wait? | Wheel of Wisdom

I love putting popular business advice to the test, because a catchy sentence can still lead your business in the wrong direction. In this episode, Jonathan and I spin th

$400 Million of Growth, Then Chapter 11

I have seen business owners celebrate rising revenue while wondering why the bank account still feels empty. In this episode, Jonathan and I look at Restaurant Dive's rep

Your Best Quarter Can Still Leave You Broke | Monday Mindset

A business can have its best sales quarter ever and still struggle to cover payroll when customers have not paid their invoices. In this Monday Mindset episode, I start w

Gusto vs. QuickBooks Payroll: My Pick for a Small Team | Software Saturday

One missed payroll notice can turn into a cash-flow headache, and choosing payroll software does not make payroll risk-free. I open with a small-business owner's $25,000

Your P&L Is Trying to Tell You Something | Friday Fundamentals

I am breaking down a profit and loss statement so you can stop treating financial language like a secret code. Using a fictional construction company, I walk through reve

Stop Pricing Service Work by the Hour

A first-year landscape design and build owner estimated a small paver reset at about $750, but worried that even $600 was too much for work that felt simple. In her updat

Cash in the Bank Does Not Mean Profit | Wheel of Wisdom

An impressive bank balance can hide bills, subcontractor payments, or other obligations that have not cleared yet. On this Wednesday's Wheel of Wisdom, Jonathan and I tes

Nearly $2 Million in Revenue, Still Can't Quit the Day Job

A business can grow from $180,000 to nearly $2 million in annual revenue and still leave its owner unable to quit an outside job. I read a Reddit post from an e-commerce

Your Business Partner Is Spending the Company Money | Monday Mindset

I want to start this Monday by asking where unresolved hurt, fear, or resentment is showing up in your business. I share how an emotional reaction to an out-of-scope requ

Can Claude Really Do Your Bookkeeping? | Software Saturday

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 replaceme

The Business Pays Her, But She Cannot Face Another Email | Freedom Friday

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 profitabili

What Does a Bookkeeper Actually Do? The Work Behind Clean Books

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

All Debt is Bad Debt? Business Advice True/B.S. | Wheel of Wisdom

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. So

Their $171,000 Tax Bill Was Wrong

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.