Marti DenUyl - Certified QuickBooks ProAdvisor

Paid a contractor $600 or more this year for repairs, lawn care, cleaning, anything like that? A 1099 might be required, and the deadline to send those out is the end of January.

The part that trips people up isn't the form itself. It's not having the contractor's W-9 on file, so come January there's a scramble to track down a tax ID or address for someone who did one job back in March. Getting a W-9 signed before paying a new contractor solves this before it becomes a problem.

Every state has its own rules for charitable registration renewal. The deadlines rarely line up with anything else on a nonprofit's calendar, and missing one can mean penalties or even a suspension of fundraising privileges until it gets sorted out.

Pull up your state's charity registration status this week. Confirm the renewal date. It's usually annual, but the exact timing depends entirely on where you're registered.

September 15 will be here soon. Q3 estimated taxes are due, and the business owners who feel the pinch hardest are usually the ones who didn’t set anything aside as the quarter went along.

A simple move: every time you get paid, pull a percentage of income and place it into a separate savings account, even a rough estimate. Doesn’t need to be exact. Having something set aside beats scrambling in September to come up with the full amount at once.

Plenty of business owners keep refining a plan long before anyone else sees it. I've done this myself more than once. A tweak here, a rewrite there, and somehow the thing never quite leaves my desk.

A version at ninety percent would've already been in the world, making money, getting better through real use instead of endless tweaking alone. This isn't a quality problem. It's just human nature to keep wanting to fix one more thing, and that instinct rarely knows when to stop on its own.

Perfect doesn't exist anyway. Finished does.

Every accountant has a calculator they're weirdly loyal to. Doesn't matter how old it is or how many buttons have worn smooth. Try to hand them a shiny new one and watch the reaction.

There's no real explanation for it. It's just the one that feels right.

Using a property manager? There's a trust account somewhere holding your tenants' rent before it gets sent over to you. That account isn't the same as your regular operating account, and it needs its own separate reconciliation.

A lot of investors just fold those transactions into their regular books. Security deposits end up mixed with income. Reserves held back for maintenance disappear into the wrong bucket. None of it looks wrong right away. It shows up later, usually as a number that doesn't make sense and takes a while to trace back.

Get a monthly statement from the property manager. Reconcile that account on its own.

The business owners with the cleanest books rarely spend more time on bookkeeping than everyone else. They just spend time on it more often.

Fifteen minutes, once a week, looking at what came in and what went out. That’s it. No deep dive, no full reconciliation, just a quick pass so nothing sits for two months turning into a mess.

Put it on the calendar like any other recurring meeting. Future you, staring down tax season, will be relieved you did.

Twelve years into running this practice, and I still catch myself appreciating stages I used to just want to get through.

Those first couple years were mostly me scraping together clients any way I could. Then came a much longer stretch of just quietly building trust, one closed month at a time. At one point growth outran my own systems and I had to rebuild how I worked from the ground up.

None of it felt like success while I was in it. Looking back, every part of it built the person running this business today.

Wherever you are in your own business right now, even the hard stretch, it's doing more for you than it feels like.

My idea of an exciting Friday is finding the error that's been throwing off a reconciliation for the last hour.

A new roof and a leaky faucet don't belong in the same category in your books, but I sometimes see them lumped together. Repairs get written off the year you pay for them. Capital improvements get spread out over several years through depreciation.

The rule of thumb: if it restores something to its original condition, that's a repair. If it makes the property better, bigger, or extends its life, that's a capital improvement. New paint, patching drywall, fixing a leak, all repairs. A new roof, a room addition, a full kitchen remodel, all capital improvements.

Set up separate accounts for each in your bookkeeping software from the start. Sorting this out after the fact at tax time is the hard way to learn the difference.