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  • Writer's pictureLindsay Spiller

A Guide to Navigating Rule 144 and Section 83(b) for Startup Companies

Updated: Dec 31

A man holding a card with a question mark under the headings "Rule 44" and "Section 83(b)"
Rule 44 and Section 83(b) are a mystery to most founders.

As a business owner or startup founder, you may face a maze of legal terms and regulations, especially when dealing with securities and taxes. Rule 144 and Section 83(b) are two of the most important to understand. This blog post will demystify these regulations and highlight their significance for startups.

Understanding Rule 144

Firstly, let's talk about Rule 144. This regulation, enforced by the U.S. Securities and Exchange Commission (SEC), sets the conditions under which specific securities can be sold or resold. This is crucial for startup founders, as your equity often falls under these categories.

The purpose of Rule 144 is to protect the market and investors from unfair practices. This regulation limits how and when company insiders or major shareholders can sell their securities. It also provides a legal way to sell restricted and controlled securities that were previously difficult to trade in the public market.

The conditions set by Rule 144 include a holding period before selling (typically six months for a reporting company), the requirement for current public information about your company to be available, restrictions on the volume of securities you can sell, and requirements for the manner of sale, among others. Knowing and understanding these conditions will help you make informed decisions about the sale of your securities.

Decoding Section 83(b)

Section 83(b) of the Internal Revenue Code (IRC) is the second key provision. This rule is relevant for startup employees or founders who receive restricted stock.

In simple terms, Section 83(b) allows you to choose to pay taxes on the total fair market value of the restricted stock at the time it's granted rather than at the time it vests. This can be a significant advantage if you expect your stocks to appreciate over time.

Here's an example. Suppose you're granted 1,000 shares of restricted stock worth $10 each, for a total value of $10,000. If you make an 83(b) election, you'll immediately pay income tax on the $10,000. Three years later, when the shares vest, they're worth $30 each, for a total of $30,000. Thanks to the 83(b) election, you don't owe income tax on the more significant amount. When you sell the shares, you only pay capital gains tax on the increase from $10,000 to $30,000.

But the 83(b) election isn't without risk. If the stock value drops or if you leave the company before the stock vests, you've paid tax on income you never actually received. Therefore, it's crucial to consider these factors before deciding to make an 83(b) election.

Navigating Rule 144 and Section 83(b) for Your Startup

So, what does this all mean for you as a business owner or startup founder? Regarding Rule 144, you must be aware of the restrictions on selling your securities and understand the conditions you must meet to do so legally. Regarding Section 83(b), it's essential to understand the potential tax implications of your restricted stock. Making an informed decision about the 83(b) election involves careful analysis of your company's future growth prospects and your expected tenure with the startup.

In conclusion, navigating the complexities of Rule 144 and Section 83(b) is integral to managing your startup's equity. Understanding these regulations allows you to make informed decisions and plan for the financial future of your business. Always consult a qualified business lawyer or tax advisor when dealing with these matters. With this knowledge, you'll be better equipped to steer your venture toward success.

Spiller Law is an advisor to startup businesses, entertainment and media companies, and artists. Feel free to schedule a free consultation.


Spiller Law is a San Francisco business, entertainment, and estate planning law firm. We serve clients in the San Francisco Bay Area, Silicon Valley, Los Angeles, and California. Feel free to arrange a free consultation using the Schedule Appointment link on our website. For other questions, call our offices at 415-991-7298.


The information provided in this article is for general informational purposes only and should not be construed as legal advice or opinion. Readers are advised to consult with their legal counsel for specific advice.


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