Entrepreneurs Pay Too Much in Taxes Because They Don’t Do This
Tax planning isn't something a lot of owners of small businesses are passionate about, but for some, it could be a make-or-break proposition.


As we head deeper into tax season, we’re starting to hear from more and more Americans experiencing sticker shock as they file their returns. Gone is the comforting and often sizable refund check they’ve come to expect every year. Instead, they’re finding they’re owed much less than in previous years or, in the worst cases, are in debt to Uncle Sam for the first time in their lives.
There is a certain, somewhat understandable, psychology at play here. Even if their paltry refund or shocking tax bill comes in a year in which they’ve paid less in taxes overall, Americans still feel screwed when their annual windfall doesn’t arrive. Businesses are no different. For newly successful entrepreneurs, though, this same tax season despair has nothing to do with the changes to our tax laws. What connects both is a failure to plan.
Most entrepreneurs just starting out don’t have a clue that they can even do tax planning. They’ve started their business, they know they need someone to do their taxes for them, and they meet with a CPA who tells them they should be set up as a single-member LLC, which gives them liability protection.

Sign up for Kiplinger’s Free E-Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
What that accountant doesn’t tell them, in most cases, is that this may be a much more expensive way to operate, since now all of their profits are taxed as self-employment income.
That might make it easier for their accountant, who doesn’t have to file another tax return. But at the end of the year that could be a very costly mistake, because being hit with a giant tax bill doesn’t just hurt the business, it could pose a threat to its continued existence.
Typically, most entrepreneurs avoid tax planning for one of three understandable reasons, or sometimes all three at once:
- They don’t know they should do it.
- Their accountant hasn’t told them to.
- They’re terrified of the IRS, and they’re almost willing to overpay out of fear.
It goes back to the old business adage: What got you here won’t get you there. The entrepreneur has a great idea. They start their business, and soon they’re making money. That’s fantastic. But nothing can quite prepare them for a $200,000 tax bill that they weren’t expecting because they didn’t know, for instance, that it probably made more sense to set up an S Corp rather than an LLC.
They didn’t hire the right accountants for their business, perhaps because they assumed their business was too small to need that sort of pricey advice. At the time, hiring a friend or the guy who had handled Mom and Dad’s returns made sense. Now it no longer does. The worst part: The problem only gets bigger as their company gets more successful. What should feel like a win instead feels like a loss.
And what of that giant tax bill they weren’t expecting? More often than not, they’ll pay it once, twice, maybe even three times before they ask the right questions and learn that there are ways they can avoid these kinds of surprises.
In the meantime, those big tax bills are cutting into working capital, depriving the entrepreneurs and the business of the one thing they need to compete and continue growing. If they write a large check enough times, they’ll eventually get frustrated and do something about it — assuming they haven’t paid so much that their very business is at risk.
It’s never too late for entrepreneurs to start planning. And it all begins with one, straightforward question: What can I do to reduce my tax bill? If the accountant’s response is that they’re already doing everything they can do, it’s probably time to find someone else.
New businesses don’t know what they don’t know. If an entrepreneur trusts someone enough to set up their company, they probably trust that person enough to save them the maximum amount come tax time. They think they’re protected. They think they're invincible. And, unfortunately, that sort of thinking ends up costing them a lot of money.
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.

Bruce Willey has been working with small to midsize businesses across the country for more than a decade, helping them navigate business and tax law in a variety of situations. His services include assisting with business start-ups, operations, growth, asset protection, exit planning and estate planning.
-
I’m a 61-year-old widow who’s dreading retirement, but I can’t work forever. What’s my move?
Retirement can be a gloomy prospect without a partner to share it with. We've asked the experts for their take on approaching this new chapter with confidence.
-
For a Richer Retirement, Follow These Five Golden Rules
These Golden Rules of Retirement Planning, developed by a financial pro with many years of experience, can help you build a plan that delivers increased income and liquid savings while also reducing risk.
-
Five Ways to Adapt Your Charitable Giving Strategy in a Changing World: An Expert Guide
Economic uncertainty, global events and increasing wealth are shaping the charitable landscape this year. Here are the philanthropic trends and some tips that could help affluent donors optimize their impact.
-
Six Big Beautiful Opportunities: Advisers' Guide to Tax and Client Strategies
Here are several ways financial professionals can help their clients maximize opportunities in the One Big Beautiful Bill Act, which extends key TCJA provisions, introduces increased deductions for people 65 and older and more.
-
Five Ways to Maintain Charitable Giving During Volatile Times: A Giver's Guide
When the economic outlook is uncertain, charitable giving is even more important — and impactful. You can be strategic by using donor-advised funds, diversifying assets and prioritizing unrestricted gifts.
-
You Don't Have to Be Wealthy to Need a Wealth Manager
Navigating complex financial decisions is hard on your own, no matter how much money you have. A wealth manager can provide comprehensive financial planning, investment management, risk management and more.
-
Five Things to Consider Before Rolling Your 401(k) into a Roth IRA
Converting at least some of an old 401(k) to a Roth IRA can offer long-term tax benefits and retirement flexibility, especially if you anticipate being in a higher tax bracket later or wish to leave a tax-free legacy.
-
Selling Your Business? This Powerful Insurance Option Unlocks Multigenerational Wealth
Private placement life insurance (PPLI) offers almost unbelievable investment flexibility, estate planning and tax advantages. And it's completely legit.
-
Retirement Tax Bombs: How Roth Conversions May Cut the Blue Wire
If you have a significant amount in tax-deferred retirement accounts, you could be sitting on a tax time bomb. Luckily, there's a way to defuse the situation.
-
Ready to Retire? Your Five-Year Business Exit Strategy
If you're a business owner looking to sell and retire, it can take years to complete the process. Use this five-year timeline to prepare and stay on track.