Small Business

The 5 Unexpected Legal Issues in Business that You Need to Avoid

September 4, 2017
5 min read
Distraught business woman reading mail
Get the legal advice you need without the hourly legal fees
Explore Plans

“Entrepreneurs are crazy,” says Steve Blank, business guru and author of The Startup Owner’s Manual. Admittedly, the challenges facing entrepreneurs are daunting. As reported in the Arizona Republic, nearly 2 in 5 business owners have come close to failing. In fact, 13% said that they had previously owned a business that had failed. Additionally, nearly 2/3 of them report that “being a small business owner or entrepreneur takes more work than they expected.”

Despite these enormous challenges, the vast majority of them (96%) reported that they were glad that they had become an entrepreneur. This is why Blank suggests that:

"(Entrepreneurs) are insanely driven to bring that thing they see to fruition. And they need to be because of the amount of travails they go through in making something out of nothing. Founders create on a blank canvas; founders are closer to artists than they are to engineers or business people. They make things happen. And they need this perseverance and tenacity and resilience to drive them through those obstacles because rationally, it would make a lot more sense to just exchange your labor for money.”

Given their risk-taking nature and fast-paced work style, entrepreneurs can struggle with legal issues that result from poor planning. In his law practice, attorney Michael E. Fiffik, from Welch, Gold, Siegel & Fiffik, P.C. in Pittsburgh, a LegalShield provider law firm, sees five major legal issues that consistently face his entrepreneurial clients.

Top 5 unexpected business legal issues

1. Unfair contracts

“Every business owner has relationships governed by contracts, from lenders to suppliers to customers to employees. Business owners should always try to dictate the relationship’s terms by using their own contract. One example is purchasing materials or supplies; entrepreneurs should avoid using a vendor’s order form and create their own purchase orders with terms that are more favorable to them. The vendor may be anxious for the sale and agree to use your form instead of theirs. In the event of a dispute, your terms will offer you important protections. Which is exactly why, if you must use someone else’s contract, reading it is an absolute must. Vendors will often include very unfavorable terms in their agreements such as high interest rates on unpaid balances, personal guarantees, specifying that dispute will be governed by the law of a different state, etc. Any one of these can cripple a small business.”

2. Inadequate protections for financial information

“Business owners should guard their financial information very carefully, both inside their business (from employees who can use the information on behalf of a competitor or to share sensitive data with customers) and outside (for example, from people who might obtain a judgment against the business and then place a freeze on accounts that they are aware of). Consider using a bill-paying account that is funded with only enough money to pay the bills. Keep your cash reserves in a completely different bank.”

3. Mistakes in wage payments

“These are very common and include problems such as making illegal deductions from employees' pay for cash drawer shortages, uniforms and customer walkouts. Other issues include not compensating appropriately for overtime and mishandling tips and the tip credit. These errors almost always arise from a lack of understanding of the applicable wage laws, which can hit employers with back pay, interest, penalties and attorneys’ fees for claims filed by current or former employees. In addition, owners can be held personally responsible for unpaid wages.”

4. Handshake deals

“My grandfather was a banker at a community bank in Masontown, Pennsylvania and used to make loans on handshakes. Handshakes are important – psychologists have studied it! You can really size up a person from the way they shake hands. The nostalgia of the “handshake deal” is wonderful but the times have really changed. In today’s electronic B2B world, many business people never meet one another. In a world where first impressions are becoming harder to come by, my advice is ‘get it in writing.’ If you’re willing to say it, then put it on paper. If they will not, it may be one of those deals better avoided.”

5. Inadequate insurance

“Events that lead to insurance claims are, by their very nature, unexpected. Some business owners want to risk ‘doubling down’ on the risk by not having adequate—or sometimes any—insurance. In some instances the law requires insurance—workers' compensation, builders risk insurance being two common types. Not having adequate insurance for a property investor can be a disaster that is one freak accident away. One of my clients had a rental property that caught fire due to a tenant’s over-heated laptop left on a carpeted floor. He found out the hard way that his insurance wasn’t up to par, costing him thousands of dollars in lost revenue because he is unable to afford to repair the property.

Another client let his workers' compensation insurance lapse before one of his employees was clipped by a driver and seriously injured. Thousands of dollars and fines were incurred as a result of medical bills, lost wages and government investigation. It pays to find a good insurance broker, take the time to explain the nature of your business to them and be engaged in the process of shopping for insurance that will cover the likely risks associated with your business.

Get the Answers You Need,
When You Need Them

Shop Plans
Share this article
Label
Label
Label
Label

Related articles

Back to Learning Center
Two women shaking hands during a business meeting
Small Business
5 min read
How To Franchise Your Business: A Six-Step Overview

Knowing how to franchise your business takes more than enthusiasm. It takes documented systems, legal preparation, and the right partners.

5 min read
Person avatar icon.
Author Name
,
Author Title
June 17, 2026
A person wearing an apron holds open the door to a cafe and flips around the "open" sign in the window.
Small Business
6 min read
How to Transfer Property to an LLC: A 5-Step Guide

In this guide, we walk you through how to transfer property to an LLC in just a few steps, along with key things to watch for so you can make this change with clarity and confidence.

6 min read
Person avatar icon.
Author Name
,
Author Title
June 15, 2026
A man filling out business documents.
Small Business
9 min read
How To Create an Anonymous LLC: A Step-by-Step Guide to Business Privacy

It’s not available in every state, but certain jurisdictions allow you to form an LLC without listing members or managers in publicly searchable records.

9 min read
Person avatar icon.
Author Name
,
Author Title
June 15, 2026
A high-end apartment building with palm trees. The sky is clear and blue.
Small Business
5 min read
A Guide to Starting an LLC for Real Estate

We’ll talk about how to start an LLC for real estate, and go over some concerns about personal liability in case something goes wrong.

5 min read
Person avatar icon.
Author Name
,
Author Title
June 12, 2026
A bakery owner reviewing documents on a laptop.
Small Business
6 min read
How To Get a Business Name: 4 Common Methods

The naming process can involve up to four different methods. We’ll describe what these methods are and how to use them.

6 min read
Person avatar icon.
Author Name
,
Author Title
June 12, 2026
People packing up an office to move.
Small Business
6 min read
How to Move an LLC to Another State: Your Options Explained

There are generally four approaches: domestication, foreign qualification, dissolution/formation, and merger. Let’s take a closer look and discuss how you can prepare before the move.

6 min read
Person avatar icon.
Author Name
,
Author Title
June 10, 2026
Two professional women talking in an office.
Small Business
5 min read
5 Advantages of Incorporation for Your Business

Incorporation is the legal process of turning a business into a “legal person” that’s separate from you. An incorporated business can own property, pay taxes, and sign contracts under its own name.

5 min read
Person avatar icon.
Author Name
,
Author Title
June 5, 2026
Two businesswomen discussing their small business
Small Business
8 min read
Registered Agent Responsibilities: What Do They Do?

Your registered agent is your business’s official point of contact, and you need one in every state where your company is formed or registered.

8 min read
Person avatar icon.
Author Name
,
Author Title
June 4, 2026
*See your plan contract for details. Additional fees, limitations, and waiting periods may apply.