What's the matter, pumpkin? Tax season was a big, flaming dumpster fire full of poo? I get it – as someone who is mentally incapable of focusing on spreadsheets for more than 7 minutes per year, I used to get some pretty nasty piles of IRS poo thrown at me regularly. Don't get me wrong, the IRS still throws plenty of poo, but I'm able to dodge more of it than ever because I have a tax strategist (in addition to my CPA and bookkeeper). (No, this isn't a pitch, I'm not even going to mention her name.)
Here's the reality most small business owners don't love hearing: You're probably not overpaying taxes because the system is unfair. You're overpaying because you're playing defense instead of offense.
Tax strategy isn't about scrambling in April.
It's about making smart moves all year long.
Yeah, I know...that doesn't really help you at this very moment, but I want to help you for next tax season. Pro tip: your tax strategist might be able to revisit your past years' filings and resubmit them to get some of that cash back in your pocket that your CPA overlooked (your CPA isn't being a weenie, it's just a completely different expertise – like a regular cake baker vs a wedding cake designer). (great…now I want cake).
Below are 17 lesser-known strategies inspired by my tax strategist with actual context so you can see if they fit in your world. These are in order of my favorites.
I'm not a tax professional, I do not play one on TV, and this is not tax advice. Every situation is different, and tax rules change. Before implementing any of these strategies, talk with your CPA or a qualified tax strategist who understands your specific business and goals.
The IRS Audit Risk
That's my official "how much trouble could this get me in if I get sloppy?" scale.
- One little 💩 = pretty safe if you follow directions
- A few 💩💩💩 = you'll want documentation and a clue
- Five 💩💩💩💩💩 = this is where people say "I'm sure it's fine" right before it is, in fact, not fine
It's not about avoiding these strategies. Some of the biggest savings live in the higher 💩 categories.
It just means... maybe don't freestyle your way through those.
The 17 Strategies
1. The Augusta Rule (Rent Your Home to Your Business) 💩💩💩
This one is a doozy! It allows you to rent your personal residence to your business for up to 14 days per year without claiming that income personally. Meanwhile, your business gets to deduct the rental expense.
This works especially well for things like team meetings, planning days, or even filming content. The key is documenting fair market rent (calling three hotels in the area and getting a legitimate average of what they'd charge you per day to rent similar-sized space). It also has to be a legitimate business purpose. If you're already hosting strategy days at your house, you might as well get paid for it! You can thank me later.
2. Hire Your Kids (Even Younger Than You Think) 💩💩💩💩
If your kids can legitimately contribute to your business (think your six-year-old organizing things or your teen scheduling posts or helping with basic admin), you can pay them and shift income out of your higher tax bracket.
I did this when my youngest was 10 and wish I had known about it sooner. I also deducted expenses on non-essentials (think cell phones, summer camps, even college tuition) from their wages, so they actually saw very little cash… which they were thrilled about, obviously.
That income may be tax-free up to the standard deduction. It's one of the few ways to move money inside your family while reducing taxes and teaching your kids how money works.
But… this is one the IRS actually watches. Your child cannot be your "Director of Global Strategy." They need to be doing real, age-appropriate work, paid a reasonable market wage, and documented like any other employee. This is not a DIY situation.
3. Accountable Plan (Most People Miss This) 💩
I do this one religiously, every quarter. Instead of paying for business expenses personally and hoping they "count," an accountable plan allows your business to reimburse you properly. Which sounds boring… until you realize how many people are doing this wrong. This keeps reimbursements tax-free to you and deductible to the business. It also cleans up your books and makes you look like a responsible adult, which is always a nice bonus.
A lot of business owners skip this and either miss deductions or create a paper trail that would make an auditor very curious.
4. The "Administrative Office" Strategy 💩💩💩
If your home office qualifies as your principal place of business, this one can unlock a lot. For example, travel from your home office to other work locations can become deductible. That's a big shift compared to normal commuting, which is not deductible at all. This is especially useful if you're doing what I do—working from home most of the time and going somewhere else (studio, office, etc.) for specific tasks.
But this only works if your home office is legitimately your administrative hub. Not "a desk you occasionally sit at while scrolling."
5. Buy a Business Vehicle the Smart Way (Not the Obvious Way) 💩💩💩
You may have heard about writing off big SUVs. That's the headline version. The real strategy is way less sexy and way more effective. It comes down to choosing the right combination of lease vs purchase, how you depreciate it, when you buy it, and what percentage is actually business use. This one definitely required a conversation with my strategist, because it's more complicated than you think. Also, and I cannot stress this enough, driving to and from work is not business use. That's commuting. Yes, even if you own the business. (I know. Rude.)
Ask your tax strategist: "Given my income this year, what's the smartest way to structure this purchase?" If they can't answer clearly, back out of their office slowly, but do not break eye contact.
6. Medical Expense Strategy (HRA / Section 105) 💩💩
Through certain reimbursement plans, your business can cover medical expenses for you and your family. We're talking insurance premiums, out-of-pocket costs, all of it. And in many cases, it becomes fully deductible to the business. This is one of those "why isn't everyone doing this?" strategies… until you realize it requires actual setup and compliance.
Done right, it's clean and powerful. Done casually, it's confusing and easy to mess up.
7. R&D Tax Credit (You Probably Qualify) 💩💩
If you're improving processes, testing systems, or experimenting in your business, you may qualify for the R&D tax credit. No, you do not need to be building robots. Marketing tests, operational improvements, and trying new ways of doing things can all potentially count. This is a credit, not just a deduction, which means it directly reduces what you owe.
Where people get into trouble is stretching the definition of "research" into "we tried something once and it didn't work." Let's stay grounded.
8. Prepay Expenses (But Only When It Actually Helps) 💩💩
You can prepay certain expenses like rent, insurance, or software and deduct them now. Sounds great… until you realize timing matters. If next year is shaping up to be a higher-income year, you may actually want that deduction later, not now.
This is less about the tactic and more about thinking ahead, which I realize is deeply inconvenient.
9. Income Shifting Through Family Ownership 💩💩💩💩
Bringing a spouse or family member into ownership can open up real tax planning opportunities. It allows income to be spread across multiple taxpayers instead of sitting in one high bracket. It can also expand retirement contribution options. Also, and I say this with love: do not do this if your relationship is even slightly questionable long-term. Ask me how I know.
Like everything else on this list, it has to reflect reality. Not just paperwork you hope holds up.
10. Retirement... But Not the Boring Way 💩💩
Basic retirement plans are fine. But as with many things in life, higher-income business owners can often do much more. Cash balance and defined benefit plans can allow for significantly larger contributions, sometimes into six figures. That means larger deductions now and more money set aside for later.
This is where tax strategy quietly turns into wealth strategy… which is a much more interesting conversation.
11. Depreciate Your Website (Almost Nobody Does This Right) 💩
Your website isn't just an expense. It's an asset. Depending on how it's built, you may be able to amortize or accelerate parts of the cost instead of just expensing it and moving on.
Is this the biggest lever on the list? No. Does it add up over time? Absolutely.
Also, it's one of those things almost nobody asks about.
12. Travel... Structured Correctly 💩💩💩💩
Business travel is deductible… when it's actually business travel. You need:
- A clear business purpose
- Proper documentation
- The right split between business and personal days
You can combine business and personal travel, but the business portion has to stand on its own.
The IRS does not care that you "thought about work" while sitting by a pool.
13. Charitable Giving With Strategy (Not Emotion) 💩💩
Donating cash is simple. It's just not always the smartest move. Donating appreciated assets or using donor-advised funds can increase your deduction while preserving more of your actual cash.
Same generosity. Better math.
14. Inventory Write-Down Strategy 💩💩💩
If you carry inventory, you may be able to write down items that are obsolete, damaged, or unlikely to sell. This reduces your taxable income by acknowledging reality: it's not worth what you paid for it anymore. A lot of businesses avoid doing this because it feels like admitting defeat.
The IRS, however, loves accuracy.
15. State Tax Arbitrage 💩💩💩💩💩
Where you live and where your business operates can have a big impact on your tax bill. With the right structure, some businesses can reduce exposure to high-tax states. There's a reason certain states are packed with corporations.
This is powerful… and also where things get complicated fast. Do not wing this. This is absolutely a "bring in experts" situation.
16. Timing Income on Purpose 💩
Depending on your accounting method, you may have some control over when income is recognized. You can delay invoices, accelerate collections, or shift timing between years to land income where it's taxed more favorably.
This is one of the simplest strategies conceptually… and one of the least used. Mostly because it requires paying attention before December 31.
17. Build a Tax Strategy Team (Not Just a Tax Preparer) 💩
There's a big difference between someone who files your taxes and someone who helps you plan them. A preparer reports what already happened. A strategist helps you decide what should happen. If you only have the first one, you've just got yourself a plain peanut butter sandwich without the jelly.
And NO, your strategist doesn't have to be from your state. We're talking mostly federal taxes.
Your Next Move
Don't try to implement all 17. Pick a few that actually apply to your business and have a conversation with your CPA this quarter, not next tax season.
If your CPA has that glazed, deer-in-headlights look…it's time to bring in a tax strategist.