Deciding on a legal entity is among the most vital choices a founder makes, yet many treat it as a mere formality. Often, entrepreneurs rush through this step at formation or let an online filing service handle it with a few clicks. Unfortunately, this hasty approach can become incredibly expensive as the business grows.
In this special “Legal Roleplay” episode of Letters of Intent, Carbon Law Group founders Pankaj Raval and Sahil Chaudry break down entity selection through a simulated consultation. Rather than focusing on abstract theory, they address the practical questions founders actually ask. For instance, they explore how taxes really work, the dangers of “phantom income,” and why healthcare businesses must follow a different set of rules.
This guide expands that conversation into a roadmap for small and growing businesses. Whether you are launching, restructuring, or preparing for investors, your entity choice dictates your taxes, liability, and eventual exit.

Why Entity Selection is a Strategic Decision
Many founders form an entity simply because a bank or investor demands it. While these are valid reasons, entity selection is really about where your business is going, not just how it starts.
Specifically, your choice affects:
-
Cash Flow: It determines how money moves through the business.
-
Taxation: It dictates how and when you pay the IRS.
-
Scalability: It controls how easily you can bring on investors or change ownership.
Think of it like choosing a vehicle:
-
LLC: A flexible pickup truck—easy to operate and great for early hauling.
-
C-Corp: A high-performance vehicle built for speed and outside capital.
-
S-Corp: A fuel-efficient commuter car that thrives once profits stabilize.
Choosing a vehicle based on today’s needs instead of tomorrow’s destination is a common mistake. Consequently, many businesses get stuck when taxes surprise them or investors hesitate because the foundation was built for a smaller operation.
LLCs and the Hidden Trap of “Phantom Income”
LLCs are popular because they are simple and offer pass-through taxation. However, this “benefit” can quickly become a trap known as phantom income.
In an LLC, the business itself doesn’t pay income tax; instead, profits pass through to the owners. As a result, you must pay taxes on your share of the profit even if the money remains in the business account. For example, if your LLC earns $500,000 and you reinvest it all, you might still personally owe $180,000 in taxes without having the cash on hand to pay it.
Furthermore, LLC owners generally face self-employment taxes on their share of income. While LLCs are excellent for early-stage or lifestyle companies, they can become a strategic burden if you plan for heavy reinvestment or outside capital.
C-Corporations: Built for Venture Capital and Scale
Despite their reputation for “double taxation,” C-Corps are often the best structure for aggressive growth. Because profits can stay within the company without triggering personal tax for founders, they effectively solve the phantom income problem.
Moreover, C-Corps are the “language of investors”. Most venture capital funds and institutional investors require a C-Corp structure for:
-
Standardized Equity: Easier issuance of stock options.
-
Clear Governance: Predictable board and compliance structures.
-
QSBS Benefits: Under Section 1202, eligible founders may exclude up to 100% of capital gains (up to $10 million) on the sale of stock held for five years.
The S-Corp Strategy for Stable Profitability
If your goal is stability and tax efficiency rather than venture capital, an S-Corp election may be the right path. An S-Corp is not a separate entity, but a tax election for LLCs or corporations.
The primary advantage here is self-employment tax savings. By paying yourself a “reasonable salary” and taking the rest of the profits as distributions, you can avoid self-employment tax on a significant portion of your income. This strategy is particularly effective for professional service providers and agencies that do not intend to raise outside capital.
Healthcare and the MSO Model
Healthcare founders face unique regulatory hurdles, such as laws that prevent non-doctors from owning medical practices. To bypass these restrictions while remaining investable, many founders utilize a Management Services Organization (MSO).
In this model, the clinical entity is owned by licensed professionals, while the MSO handles operations like marketing, billing, and technology. This allows investors to fund the MSO without violating medical ownership rules. However, because MSOs are legally complex, they require carefully drafted agreements to avoid regulatory violations.
How Entity Choice Impacts Your Final Exit
Finally, your entity selection directly affects your company’s valuation. Buyers look for:
-
Clean Financials: Standardized structures they already understand.
-
Transferable Ownership: Ease of diligence and transition.
-
Predictability: Documented governance and clear equity.
Ultimately, a business built entirely around one owner without a scalable structure is much harder to sell. By choosing the right foundation now, you ensure that your business remains an asset rather than just a personal job.
The Bottom Line
Choosing between an LLC, C-Corp, or S-Corp is not about what is easiest today; it is about what works tomorrow. Because every growth phase brings new legal and tax consequences, making an intentional decision now will prevent expensive resets later.