Even the most successful business owners can leave thousands—or even millions—on the table by overlooking tax planning. And no, we’re not talking about shady deductions or risky loopholes.
We’re talking about the everyday mistakes that happen when your tax, legal, and financial strategies operate in silos. At Alperin Law & Wealth, we help business owners avoid these traps by building proactive, integrated plans that align with your business growth, personal wealth, and long-term legacy.
Mistake #1: Waiting Until Tax Season to Start Planning
The most common tax mistake? Thinking planning only happens in March or April. By then, most opportunities are already gone. Real tax planning happens before the year ends—and evolves with your business all year long.
Imagine you sell a rental property in December without checking in with your advisor. The sale triggers a large capital gain that could have been minimized or offset with earlier planning. If you had reviewed your income, losses, and timing options back in the fall, you could have structured the sale more strategically and potentially reduced your tax bill.
Our proactive approach to tax planning isn’t about reacting to deadlines. It’s about making informed decisions in advance—so you stay in control, not the IRS.
Mistake #2: Choosing the Wrong Business Entity (and Not Revisiting It)
Many business owners choose a structure when they launch, but never revisit that choice as their business evolves. Unfortunately, the wrong entity can quietly cost you thousands each year in avoidable taxes.
Let’s say you’re still operating as a sole proprietor or single-member LLC. Without realizing it, you could be overpaying self-employment taxes on all your income. With the right guidance, electing S-corp status might allow you to split income between salary and distributions to lower your overall tax burden and keep more money in your pocket.
Choosing the right business structure isn’t a one-time decision. It should reflect your current income, your growth goals, and whether you're planning to sell, scale, or pass the business on to family. If your entity hasn't changed, but your business has, we can help you take a second look.
Mistake #3: Overlooking Retirement Contributions and Other Tax-Deferred Tools
Retirement planning isn’t just about the future. It’s one of the most effective tax strategies available to business owners right now. But too many business owners miss out by failing to take advantage of tax-deferred options.
For example, if you’re earning a strong income but haven’t set up a SEP IRA, Solo 401(k), or defined benefit plan, you’re paying taxes on money that could have been deferred—or growing tax-free inside a retirement account. With the right plan, you can reduce your taxable income today while building wealth for tomorrow.
And the benefits don’t stop with you. When integrated into a broader compensation strategy, these tools can also help you attract and retain high-performing employees—making them a win for both your tax plan and your business.
Mistake #4: Not Coordinating Tax Planning With Estate and Investment Strategies
Tax planning in a vacuum creates avoidable friction.
- Your investment advisor harvests gains, but your CPA doesn’t offset them with losses.
- Your estate planning attorney creates trusts that generate unintended tax consequences.
- You sell a business without a pre-sale tax strategy, which results in unnecessary capital gains or estate taxes.
At Alperin Law & Wealth, we bring these pieces together under one roof. That means no more finger-pointing between your CPA, attorney, and advisor. Just a unified plan that works.
Mistake #5: Deducting Expenses Without a Strategic Framework
It’s easy to fall into the trap of trying to write off as much as possible before year-end. But deducting expenses without a clear strategy can actually hurt more than it helps—especially if it disrupts your long-term tax planning.
For example, buying equipment in December just to lower this year’s tax bill might feel productive. But if next year’s income is projected to be significantly higher, that deduction could have been more valuable later. Smart planning means aligning your deductions with your overall income trends—not just chasing short-term relief.
On the flip side, many business owners miss out on deductions they’re entitled to—like home office expenses, vehicle mileage, or business meals—because they aren’t tracking them properly. Whether you’re over-deducting or under-claiming, the result is the same: you’re not getting the full benefit of the tax code.
Mistake #6: Failing to Plan for an Exit or Succession
Every business will eventually transition—whether by sale, retirement, or inheritance. Without proactive tax planning, the exit can be more costly than it should be. With the right trust structures, income deferral strategies, and gifting plans, you can preserve more of your sale proceeds and reduce taxes for your heirs.
If you’re within five to 10 years of exiting your business—or even just thinking about it—it’s time to start succession planning. The earlier you begin, the more control you’ll have over the outcome.
Plan Ahead to Protect More
Most tax mistakes aren’t made on purpose. They’re made because no one is looking at the whole picture.
At Alperin Law & Wealth, we help business owners build coordinated strategies that cover legal, tax, and financial planning in one place. Whether you’re launching, growing, or preparing to exit, we’ll help you reduce taxes—not just file returns.
We serve business owners and professionals throughout Hampton Roads—including Virginia Beach, Norfolk, Suffolk, Chesapeake, and Portsmouth—and into Northeastern North Carolina, including Moyock and the Outer Banks.
Schedule your discovery meeting and make tax planning a year-round advantage—not a seasonal scramble.
