In the News
Your Structure Is Only as Good as Last Month's Bookkeeping (Your Numbers are Talking)
Three entities and one checking account is never a good idea. Especially in cannabis.
That’s what I found when I opened a new cannabis client’s books, and what made it worth writing about is that the structure itself was right. An attorney had built it.
Waiting on Rescheduling Isn't the Same as Doing Nothing (Your Numbers are Talking)
Most of the cannabis operators I talk with have settled into a wait-and-see posture on rescheduling, and I understand why. The last two years handed this industry several moments that looked like the moment, and each one arrived with a wave of advice about what to do immediately.
He Thought He Was Profitable. The Numbers Said Otherwise. (Your Numbers are Talking)
He came in with a specific question: “Is my pricing set up the right way?”
The business had been in the family for years. They had a good reputation, steady clients, and consistent revenue.
But he had a nagging feeling he couldn’t shake. He thought he was making money. He just wasn’t sure.
Pricing Problems: Why Your Margins Don’t Add Up (Your Numbers are Talking)
I hear some version of this more than almost anything else:
“I think I’m making money. But I’m not sure.”
It’s not a cash flow problem or revenue problem. The business is busy, the invoices are going out, and on paper, things look okay.
But something doesn’t feel right.
The $13,000 Tech Stack Nobody Was Watching (Your Numbers are Talking)
The call came in on a Tuesday.
A new client shared that one of their key employees had a major accident and was in the hospital, completely unreachable.
Outside of the obvious concern she had for her colleague, there was one major problem: the colleague had been the one who set up most of their software, including payroll for the small business of 17 employees.
Subscription “Stacks” That Drain Your Financial Picture (Your Numbers are Talking)
I come in to look at the books.
That's usually how it starts. A business owner wants a cleanup, a fresh set of eyes on their finances, or a clearer picture of where they stand.
But almost every time, I end up looking at their tech stack too, because the tools are always part of the story
The Deal That Almost Fell Apart in the Final Week (Your Numbers are Talking)
A client called me on a Tuesday. He was in the middle of acquiring a smaller competitor he’d been eyeing for years. The deal was weeks from closing.
Then the lender flagged a cluster of transactions in the target company’s books that didn’t add up. It wasn’t a huge red flag, but ultimately amounted to some sloppy bookkeeping. Some accounts hadn’t been reconciled in months!
Exit Plans Aren’t Just for Retirees (Your Numbers are Talking)
Most business owners don’t think about selling their company until they’re ready to stop working.
And by then, they’ve often already left money on the table.
Here’s the thing: an exit plan isn’t a retirement document. It’s a business strategy. And the owners who treat it that way long before they’re ready to go are the ones who walk away on their own terms.
What's It Costing You Not to Know? (Your Numbers are Talking)
A transportation company came to us with a question they’d been sitting on for a while.They operated in multiple states, had deliberately built the business over the years, and, by most measures, were doing well.
But one location had been nagging at the owner. Something about the numbers felt off… not catastrophically, just… off.The problem was, they couldn’t say exactly what was wrong.
Stop Treating Accounting Like Overhead (Your Numbers are Talking)
Most small business owners I talk to see accounting as a cost they have to pay for, like insurance or utilities.
I’d like to gently push back on that.
If accounting is just overhead in your mind, it’s probably working against you in your business.
When Cashless Creates a Cash Problem in Cannabis (Your Numbers are Talking)
One of the most consistent challenges I see in cannabis businesses has nothing to do with product or demand.
It’s money movement. Cannabis has a real cash problem.
Banking access is limited. Processing options shift. Accounts are scrutinized differently and more closely than most industries. And you’re required to keep cannabis and non-cannabis revenue cleanly separated at all times.
Cannabis Is Not Business as Usual (Your Numbers are Talking)
I work with cannabis business owners from very different backgrounds.
Some have run successful companies before. Others came into cannabis through passion for the product and the industry itself.
Both groups care about doing things right.
When Legacy Systems Become a Family Legacy Problem (Your Numbers are Talking)
A family-owned business reached out a while back for what they thought was a simple cleanup.
They were interested in working with us on long-term accounting services—and a cleanup is typically where I start.
Nothing major — just a few inconsistencies between their project management and accounting systems, both of which were dated.
Modernize Without Losing the Soul of Your Family Business (Your Numbers are Talking)
I’ve seen it many times — a family business passes the torch to the next generation, and on paper, everything looks ready for growth.
But behind the scenes, things are far more complicated.
Even after leadership changes hands, the older generation often remains deeply involved — and deeply protective. They’ve spent decades building the company from the ground up, sometimes continuing what their parents started. To them, the way things have always been done is part of their identity and legacy.
Is Your “Company Vehicle” Becoming an Unplanned Company Perk (on your dime)? (Your Numbers are Talking)
A client once came to me frustrated about rising costs, specifically related to their company fleet.
Repairs were stable. Maintenance was normal. But somehow, fuel expenses had jumped nearly 40%.
She assumed it was just higher gas prices.
But when we compared her team’s vehicle reports, the numbers told a very different story. In fact, one number stuck out — one salesperson’s fuel bill was way higher than everyone else’s.
Six Red Flags Your Finances Aren’t as Tight as You Think (Your Numbers are Talking)
I can’t tell you how many times I’ve heard this:
“We’re a small business — we don’t need all those internal controls.”
Usually, that line comes right before we find something that’s been quietly draining cash or creating chaos for months.
It’s rarely fraud.
It’s usually something smaller — a duplicate vendor payment, a missed deposit, or an account nobody’s reconciled since last summer.
When One Person Runs the Show and Why That’s Risky (Your Numbers are Talking)
I can spot the telltale signs that one person is running the whole show almost immediately when reviewing a new client’s books.
They’re entering invoices, approving payments, reconciling the bank account, and managing payroll. Outwardly, it might look like efficiency. But to me, it’s a red flag that there are some serious risks in a business
I don’t say that to scare you. I say it because I’ve seen what happens when there’s no separation of duties. Small mistakes snowball, cash flow dries up, and worse, it’s easy for fraud to slip through undetected.
Woodard Feature: Looking Beyond the Resume to Hire a Remote Team
I’ve been remote for years, and hiring remote team members almost as long. Like the hiring process, there are some must-haves.
If there’s one thing remote hiring teaches you, it’s this: technical skills will get someone through the door. They won’t tell you if that person will thrive on your team.
Your Numbers ARE Talking
If there’s one thing I’ve learned working with small and mid-sized businesses, it’s this:
Your numbers are always talking.
But most business owners don’t know what they’re saying — or how to understand the stories they’re telling through patterns, small inconsistencies, cash flow surprises, unexplained margin dips, or processes that “mostly” work until one day they don’t.
Don’t Let Ex-Employees Keep the (Financial) Keys: Your 10-Step Offboarding Checklist
They turned in their laptop. You disabled their email. You’re covered, right?
Not even close.
When an employee leaves—whether it’s a planned departure or a sudden exit—your financial systems can be left wide open if you don’t have the right offboarding process in place.