Founder’s Guide, Part 3: Maximize Your Net Exit by Choosing the Right Entity for Your Startup
As entrepreneurs you take risks every day, one of those risks should not be tied to making a wrong decision on your entity structure. In this Part 3, we'll discuss how properly structuring your business can significantly decrease risks and increase the net value of your business. As an entrepreneur, one of the first questions that you are faced with is what kind of entity you should form. The possibilities are seemingly endless. You can go with a C-Corp, an S-Corp, an LLC, or an S-LLC. Let's explore the Pros and Cons of each type which may help you get some clarity for a decision that is not always a one-size-fits-all determination.
Pros and Cons of the Different Entity Types
C-Corp:
- Pros. The advantages of a C-Corp are the flexibility of capital structure and its attractiveness to all types of investments, both VC and debt financing. Originally issued stock in C-Corps qualify as Qualified Small Business Stock, which can result in some capital gains savings.
- Cons. The cons of the C-Corp are its double taxation. This is not a big deal when the company is generating losses, but at the time of an exit, a founder can lose serious money. Another con of C-Corps is that there are many corporate formalities requiring compliance to maintain the liability protections of the C-Corp.
- Ideal Candidate. High-growth startups wanting to attract top national VC firms or whose exit plan is through an IPO.
S-Corp:
- Pros. The pros of an S-Corp are the avoidance of double taxation as well as the ability to lessen employment and FICA taxes on owner-employees.
- Cons. The cons of the S-Corp are that it is extremely limited in its capital structure. For example, all shareholders must be individuals with a few limited exceptions for grantor trusts, and there can only be one class of financial ownership interests, which means no preferred stock. Both of these are issues that will not allow for VC financing. An additional con of S-Corps is that many corporate formalities need to be complied with to maintain the liability protections of the S-Corp. If you slip up, that slip up could result in a technical termination of the entity which could result in some pretty steep tax liabilities.
- Ideal Candidate. Small consulting or service businesses with individual owners who don’t plan on raising Venture Capital or Private Equity financing.
LLC:
- Pros. The pros of the LLC are numerous: (1) pass-through taxation; (2) flexibility in capital structure; (3) attractiveness to vast majority of potential investors; and (4) flexibility in management and lack of entity formalities.
- Cons. Disfavored by some VC investors, but with proper planning as discussed below, the adverse tax consequences can be mitigated. It doesn’t have the ability to minimize FICA taxes to owner-employees as all income is passed through to its owners.
- Ideal Candidate . LLCs are the preferred entity because they are well suited for most businesses unless your planned exit is an IPO.
S-LLC:
- Pros. The pros of the S-LLC are all of the benefits of LLC with the addition of being able to minimize FICA taxes.
- Cons. All of the disadvantages of S-Corps except the rigid corporate formalities are lessened.
- Ideal Candidate. Same as for S-Corps, but these entities are a little more flexible in entity formalities and are thus generally more favorable than S-Corps.
The following table compares the above-listed entity types:
Conclusion As you can see this is a complex decision to make and one that you should discuss carefully with both your attorney and accountant and preferably at the same time. The three takeaways from this article are the following:
- Entity structuring is not a one-size-fits-all scenario and needs to take into account many factors, including the type of business involved, its owners, and how it plans on raising money in the future. Each entity comes with its own risks.
- LLCs are oftentimes the best entity structure for entrepreneurs.
- Hire good corporate counsel early to help you take the right risks, and the few thousand dollars you spend on them could save you mountains of money at exit.
For small business owners in Utah, growing the team is an exciting milestone and you’ve likely faced the classic question: Should I hire an actual employee, or can I just find a "guy who knows a guy" and pay him via Venmo? While it might be tempting to treat an employee (W-2) and an independent contractor (1099) as interchangeable based on your budget, the IRS and the Utah Labor Commission see things very differently. Misclassifying a worker isn't just a clerical error; it can lead to significant back taxes and penalties. Here is a practical look at the differences to help you stay compliant while you scale. The Independent Contractor (1099) Think of a contractor as a separate business entity that you have hired to perform a specific project or attain a specific result. They are specialists who bring their own "secret sauce" to the table. Autonomy : They generally use their own equipment, set their own hours, and work from their own locations. The "What" Not the "How" : You have the right to control the result of the work, but not the specific methods used to achieve it. Financial Independence : They pay their own self-employment taxes, health insurance, overhead, and will typically invoice you for their services. They may have other clients besides your business. The Employee (W-2) An employee is someone who is fully integrated into your business operations. They are part of the daily rhythm of your company and are under your direct supervision. Direction and Control : You dictate when they work, where they work, and the specific sequence of their tasks. You provide the equipment to complete those tasks. Business Integration : Their services are usually a "key aspect" of your regular business activity. If your business is a bakery, the person baking the bread is likely an employee; the person fixing the oven is likely a contractor. Employer Obligations : You are responsible for withholding income taxes and paying a share of Social Security and Medicare. In Utah, you’ll also need to ensure you're covered for Workers' Compensation and Unemployment Insurance. The Bottom Line: Control The government looks closely at the reality of the working relationship , not just the title you put on a contract. Your degree of control , or lack thereof, is key. Ultimately, if it looks like a duck and quacks like a duck, they’re going to treat it like a duck. Taking the time to classify correctly now prevents headaches down the road. We are here to help you craft, review, and amend employment and contractor agreements and navigate any other issues that may arise as you scale your workforce.
AI is undoubtedly amazing. On one single platform I can direct it to, for example, “write me a 400-word blog post about the legal risks of private employees use of AI directed at Utah small to medium-sized businesses.” And then ask it to illustrate that post with an image of a robot in a skirt suit. (And now you’ll wonder if I even wrote this post myself…. I did. But I did not sketch the image myself.) And we all know AI has real limitations. We’ve heard the stories about AI hallucinations, where it simply invents an answer. And often AI simply gets it wrong. For example, I often use AI to pull up the citation to a statute and often it produces a link to a bill that hasn’t been enacted, a bill that’s been repealed, or a similar statute that’s applicable to a different industry than the one I asked it to find. But there’s also legal risks in using “Open Access” or “Free Tier” AI versus “Enterprise” or “Business” AI. Open access/free tier AI is the version you can use for free on a web browser or on app on your computer or smart phone. With many of these tools, user inputs may be stored or used to improve the model. Enterprise or business AI, by contrast, is a commercial‑grade system that typically offers encryption, enhanced privacy controls, and contractual data‑security commitments. If you do not have the latter—enterprise AI— then you really may want to find out what your employees are inputting into an unsecured AI tool. Is it client or employee information, like personally identifiable information? Medical information? Company trade secrets? Financial information? Depending on your company size and the type of information input into an unsecured AI tool, employees may be creating legal risk under Utah’s data breach notification law, the Utah Consumer Privacy Act (for businesses that meet its thresholds), federal privacy laws, even anti-discrimination laws and contractual confidentiality obligations you have made directly with your clients. The New Year is a great time to review old policies, create new ones, and train staff on these concerns. We are here to help you navigate these emerging issues! -By Adrienne Langmo
As the federal fiscal year draws to a close, thousands of federal employees face an unsettling possibility if a continuing resolution is not passed: not just another shutdown and temporary furlough, but permanent layoffs through Reduction in Force (RIF) notices. This week, the Office of Management and Budget (OMB) instructed federal agencies to consider issuing RIF notices to employees (if certain conditions are met) rather than the usual temporary Furlough notices issued during shutdowns. This is a big shift. But it does not mean layoffs are guaranteed. If they occur, federal employees are protected by a robust set of legal rights. There’s still a process before a RIF can be properly issued, complete with notice rights, retention rights, appeal rights and such other rights that the OMB does not purport to usurp. That said, we understand that the anxiety of this uncertain moment is real. Here are some tips to best prepare for the unknown, come the end of the federal fiscal year: Download Your eOPF, ASAP o Your electronic Official Personnel Folder may become inaccessible during a shutdown. Download it now to preserve your employment records. Download Your last 3 Performance Appraisals, ASAP o Include mid-year reviews and commentary. These documents may affect retention rights in a RIF. Also save records of other awards, commendations, and other notable performance records. Save Key Communications o Save emails, memos, or notices from HR or supervisors about your employment status or shutdown protocols. Ask Questions o Supervisors, HR, and union reps are navigating this too. Don’t hesitate to ask questions. If you receive a RIF notice or suspect you were subject to procedural violations, don’t hesitate to reach out to us for our advice. We are here to help. Shutdowns may be political. Your livelihood is personal. Let us help you safeguard it. -Adrienne Langmo, Partner
