Not every challenge needs outside help. Plenty of things — a straightforward budget, a simple business decision, a question you can answer with a bit of research — are entirely reasonable to handle on your own. But some situations genuinely benefit from bringing in someone with outside expertise, and it's worth knowing the difference.
People are sometimes surprised that I take the same approach to a business operations problem as I do to someone's personal financial decision. But the truth is, the type of problem matters less than the process you use to solve it. Here's the framework I rely on, regardless of what's in front of me.
Before I started my own business, before I became a REALTOR®, I worked as a finance administrator at a Fortune 500 company. It was structured, disciplined, and precise — every number had to reconcile, every report had to be defensible, and there was no room for “close enough.”
The first year or two of running a business is when a lot of financial habits get formed — some good, some that quietly cause problems down the road. Having worked in finance administration and fraud detection before running my own business, here are the red flags I'd encourage every new owner to watch for early.
Government contracts can be one of the most stable, lucrative opportunities available to a small business — but the process of pursuing them looks nothing like pursuing private-sector clients, and that difference trips up a lot of otherwise capable business owners.
Running a business with international reach is a different experience than running one that stays local, and a lot of the advice aimed at new business owners doesn't quite account for that. Having built and managed my own international business, here are five things I'd encourage anyone in this position to sort out early.
Small business owners often assume fraud is something that happens to bigger companies — organizations large enough that no single person notices when something's off. In reality, small businesses are frequently more vulnerable, precisely because there are fewer checks in place and more trust placed in fewer people.
If you've spent any time on my website, you've probably noticed a lot of language about businesses — business challenges, business goals, business success. That's real, and it's a big part of what I do. But it's not the whole picture, and I want to be direct about that.
When people think about fraud, they usually picture something happening to a company — a business accountant embezzling funds, a corporate email scam. But individuals are targeted just as often, sometimes more, and the warning signs are frequently easy to miss because they don't look the way we expect fraud to look.
Divorce. Inheritance. Retirement. A parent moving in with you, or moving into assisted living. These are some of life's biggest transitions, and they all share something in common: they arrive with financial complexity attached, often at the exact moment you have the least bandwidth to deal with it.
Business owners tend to have a particular relationship with their numbers. They don't just look at them once a year — they check in regularly, they know their trends, and they adjust before small issues become big ones. That mindset isn't exclusive to business. It works just as well at your kitchen table.
There's a common assumption that you only bring in help with your finances once something has already gone wrong — a missed payment, a mounting balance, a decision you regret. But some of the most useful conversations I have happen with people who are doing fine and just want to make sure they stay that way.
Walking into your first IEP (Individualized Education Program) meeting can feel overwhelming. You're in a room full of professionals — teachers, a school psychologist, a special education coordinator — and you're the only one there without a title. I know that feeling firsthand, because I've sat in that chair myself, advocating for my own child.
Holding a quiet stake in Smith Bookkeeping has taught me more about what real support looks like than almost anything else I've done professionally. Being a silent partner doesn't mean being uninvolved — it means being involved in the right places, and staying out of the ones that aren't yours to run.
I meet a lot of people who've been sitting on a business idea for years, waiting until they have it all figured out before they start. I understand the instinct. I just don't think it works, and I've watched it keep good ideas stuck on a shelf far longer than necessary.
Almost everyone who comes to me with a dream business starts the conversation the same way — talking about the idea, the passion, the thing they're good at. I let them finish, and then I ask a question that usually catches them off guard: “Who is this for, and what will they actually pay you for it?”
One of the things I'm proudest of isn't a listing or a client win — it's watching someone I believe in build something real. Steve had the skill and the drive to run a bookkeeping practice long before it had a name. What he needed wasn't someone to hand him a plan; he needed a partner who could help him see the business side of what he was already good at.
There's a specific moment where a side hustle becomes a real business, and it's rarely the moment people think it is. It's not when you get your first client, or even your tenth. It's when you start treating it like it has to survive without you working every waking hour to keep it alive.
Whether or not you're applying for financing anytime soon, it's worth learning to read your own numbers the way a lender does — because it's a more honest read than the one most owners give themselves.
This is one of the first questions I get from anyone establishing a new business, and the honest answer is: it depends on what you're trying to protect and how you plan to grow.
Non-negotiable, from transaction one.
I've noticed a pattern with people who own one or two rental properties: they treat it like a side project instead of what it actually is — a business, with its own books, its own risks, and its own decisions to make on purpose instead of by accident.
Almost every business plan I've reviewed gets one thing wrong: it accounts for the costs people expect and misses the ones that show up anyway.
Mixing business and personal finances is one of the most common habits I see in new business owners, and it's rarely intentional — it's just easier in the beginning. One card, one account, sort it out later. I understand the instinct. I don't recommend it.
You don't need a finance degree to run a healthy business. You need three numbers, and you need to know them without opening a spreadsheet.
If I had a dollar for every time a business owner told me they'd deal with the books “once things settle down,” I could retire. They never settle down — and by the time someone calls me, it's usually six to twelve months of unreconciled transactions and a P&L nobody trusts.
