A Deep Dive Into Regulation D and Its Strategic Use For Startups
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- July 30, 2025
A Deep Dive Into Regulation D and Its Strategic Use For Startups
Regulation D is a critical framework under the U.S. Securities Act of 1933 that allows issuers to raise capital through the sale of securities without registering the offering with the Securities and Exchange Commission (SEC). It does so by providing “safe harbor” exemptions—essentially clearly defined conditions under which an issuer can be confident that its offering qualifies for exemption from registration.
The primary objective of Regulation D is to reduce the regulatory burden and associated costs for issuers, especially startups and private companies, while still maintaining essential investor protections through disclosure obligations, limitations on resale, and restrictions on solicitation in certain cases.
Regulation D comprises three main rules—Rule 504, Rule 506(b), and Rule 506(c)—each designed to accommodate different types of issuers and capital-raising situations. These rules vary in terms of offering limits, types of eligible investors, whether general solicitation is permitted, and what information must be provided to investors. Despite their differences, all Regulation D offerings share several foundational characteristics (see below).
Overview of Regulation D
Under Section 5 of the Securities Act, any offer or sale of a security must be registered with the SEC unless an exemption applies. Regulation D provides such exemptions by defining the criteria under which private offerings are deemed compliant and not subject to the SEC’s registration process. The “safe harbor” status of Regulation D means that so long as an issuer meets the specific requirements of one of the rules, it can rely on that exemption with legal certainty.
Integration Principles
A key principle that governs all Regulation D offerings is the prohibition against integration. This means an issuer cannot divide what is functionally one offering into multiple exempt offerings to circumvent registration requirements. In practical terms, if two offerings are close in time and target similar investor groups or have overlapping marketing efforts, the SEC may deem them integrated and treat them as a single offering. If the combined offering would not meet the requirements of the exemption relied on, the issuer could be found in violation of Section 5.
To address this, the SEC has codified integration safe harbors under Rule 152, which clarify when separate offerings will not be treated as one. For instance, if a Rule 506(c) offering that uses general solicitation ends, and 30 days later the issuer launches a Rule 506(b) offering (which prohibits solicitation), the issuer must have a reasonable belief that none of the investors in the new offering were solicited during the earlier general solicitation. Failing to respect these lines can invalidate the exemption.
Resale Restrictions
All securities sold under Regulation D are considered “restricted securities” under Rule 144. This designation means they cannot be freely resold in the public markets without either registering the resale or qualifying for a resale exemption (such as under Rule 144 or Rule 144A). This restriction helps ensure that the exemption is not used as a backdoor for creating a public market in unregistered securities.
Issuers are required to take reasonable care to prevent unregistered resales. This includes:
- Placing restrictive legends on stock certificates.
- Requiring written representations from investors that they are purchasing for investment purposes and not with a view to distribute.
- Implementing stop-transfer instructions or requiring legal opinions for resales.
These measures aim to preserve the private nature of the offering and protect investors from secondary-market risks not subject to full disclosure.
A SaaS Startup Raising Series A Capital
Imagine a software-as-a-service (SaaS) startup incorporated in Delaware that seeks to raise $5 million in its Series A round. The company has received interest from venture capital firms and a few individual angel investors. To avoid the time and expense of SEC registration, the company decides to rely on Regulation D.
The offering is structured to include only accredited investors (the VC firms and a few high-net-worth individuals), but the company also considers accepting funds from a tech-savvy individual who is not technically accredited. To do this, the startup must:
- Confirm the individual is sufficiently sophisticated to evaluate the investment or has a qualified purchaser representative.
- Provide that investor with a private placement memorandum (PPM) containing detailed disclosures—including financial statements, risk factors, and the use of proceeds.
- Represent in writing that the investor is purchasing the securities for investment and not for resale.
The company also ensures there is no general advertising or social media promotion of the deal, and it files a Form D with the SEC within 15 days of the first sale.
The securities sold, as we mentioned, are restricted—meaning the VC firms and angel investors cannot flip them in a public market the next week. Instead, they must either wait to resell under Rule 144 or pursue another exempt resale (e.g., Rule 144A).
If the startup later wishes to raise another round using Rule 506(c) with general solicitation (e.g., through an online investor platform), it must be careful not to integrate that offering with the current one—especially if the second offering follows closely in time. To avoid integration, it would need to comply with the safe harbor under Rule 152 and verify each new investor’s accredited status with reasonable diligence.
Rule Comparison Summary
Rule | Max Offering Size | Who Can Invest | Solicitation Allowed | Info Requirement | Resale Restrictions |
Rule 504 | $10 million per 12-month period | Any investor | No, except for certain exceptions (see Rule 504(b)(1)) | No | Yes |
Rule 506(b) | No limit | Unlimited accredited investors + up to 35 non-accredited investors | No | Yes, for non-accredited investors | Yes |
Rule 506(c) | No limit | Accredited investors only | Yes | No | Yes |
Rule 504 – The Small Offering Exemption
Rule 504 of Regulation D is designed to provide a streamlined exemption for small-scale capital raising by early-stage or non-reporting companies. Unlike Rule 506, which allows unlimited capital raises, Rule 504 is capped at $10 million in aggregate offerings over any rolling 12-month period. This limitation makes Rule 504 especially useful for startups or closely held businesses that are in the initial phases of fundraising and do not require substantial capital injections from institutional investors.
To be eligible for Rule 504, the issuer must satisfy a narrow set of qualifications. First and foremost, it must be a non-reporting company. This means the issuer cannot be subject to the ongoing reporting requirements of the Securities Exchange Act of 1934—such as the obligation to file annual or quarterly reports with the SEC. In addition, the issuer must not be an investment company as defined under the Investment Company Act of 1940. Investment companies, such as mutual funds or hedge funds, are categorically excluded from Rule 504 due to the heightened risk and regulatory concerns they pose. Furthermore, blank check companies are also barred from using this exemption. These are entities that have no concrete business operations and are formed primarily to merge with or acquire an unidentified business in the future—raising unique investor protection issues that render them ineligible for a lightly regulated offering route.
One of the most significant constraints under Rule 504 concerns general solicitation and advertising. As a baseline, the rule prohibits the use of general solicitation in connection with the offering. That means the issuer cannot broadly advertise the offering to the public through newspapers, internet postings, social media campaigns, or public events. However, there are defined and narrow exceptions under Rule 504(b)(1) that permit solicitation in limited circumstances. These include situations where the offering is either registered in at least one U.S. state that mandates public filing and substantive disclosure to investors, or conducted exclusively in jurisdictions that allow general solicitation under a regulatory exemption that also imposes disclosure requirements. In such cases, although federal law permits solicitation, the issuer must still comply with all applicable state-level filing and investor protection obligations. Even where permitted, any general solicitation must be conducted in strict compliance with both federal and state laws to avoid losing the exemption entirely.
This leads directly to another key feature of Rule 504: it does not benefit from federal preemption of state securities regulation. Unlike Rule 506 offerings, which are deemed “covered securities” under the National Securities Markets Improvement Act of 1996 (NSMIA) and therefore exempt from state registration requirements, Rule 504 offerings remain fully subject to state “blue sky” laws. This means the issuer must register the offering in each state where the securities are offered, or qualify for and comply with a state-specific exemption. In practice, this often requires submitting a Form D, paying filing fees, and providing offering materials such as private placement memoranda to state regulators for review. The result is that while Rule 504 may seem simpler at the federal level, it can become complex and fragmented when multiple states are involved.
Despite its streamlined nature, Rule 504 does not impose specific disclosure requirements. The rule does not differentiate between accredited and non-accredited investors in this regard. However, the absence of formal disclosure obligations does not relieve issuers from liability under the federal securities anti-fraud provisions. Any material misrepresentation or omission may still trigger civil or even criminal liability under Rule 10b-5. Consequently, prudent issuers typically prepare a written disclosure document—often modeled after a simplified private placement memorandum—to describe the terms of the offering, the issuer’s business, risk factors, and financial condition. While not legally mandated under Rule 504, such documentation serves as a critical tool in managing legal exposure and demonstrating good faith compliance.
Finally, Rule 504 incorporates the “bad actor” disqualification provisions that are set forth in Rule 506(d). This means that if the issuer, or any of its directors, executive officers, general partners, managing members, or 20% beneficial owners, has been subject to certain disqualifying events—such as securities-related convictions, injunctions, or regulatory orders—the issuer may be barred from relying on Rule 504. The disqualification provisions are triggered by both recent and historical misconduct, with look-back periods ranging from five to ten years, depending on the nature of the event. Notably, even third-party solicitors or placement agents involved in the offering are covered persons under this rule. However, if the issuer can demonstrate that it exercised reasonable care and was unaware of the disqualifying event, a limited exception may apply. The burden of this proof, though, rests squarely on the issuer.
To bring this into focus, consider how our SaaS startup might use Rule 504. Suppose the startup is aiming to raise only $2 million from a mix of angel investors across multiple U.S. states and does not want the compliance burden of verifying accredited investor status. It could structure the offering under Rule 504, assuming it qualifies as a non-reporting company and is not disqualified under the bad actor rules. However, because general solicitation would not be permitted by default, the company would either need to register the offering in each state where it intends to solicit investors or structure the offering in compliance with state exemptions that permit solicitation and require disclosure. Even though no disclosure is required federally, the startup would still likely prepare a simplified investor package to avoid any claim of fraud or omission. In this case, Rule 504 offers an efficient path to early capital but demands meticulous state-level coordination and internal discipline in how the offering is communicated and documented.
Rule 506(b) – The Traditional Private Placement Safe Harbor
Rule 506(b) is the most frequently used exemption under Regulation D and provides issuers with a robust and flexible framework for raising capital without registering their securities with the SEC. Unlike Rule 504, Rule 506(b) places no limit on the total amount of capital that may be raised, making it suitable for both small-scale and large institutional offerings.
The central feature of Rule 506(b) is its investor eligibility framework. An issuer may offer and sell securities to an unlimited number of accredited investors, which includes high-net-worth individuals, financial institutions, and certain insiders such as officers or directors of the issuer. In addition, the rule permits sales to up to 35 non-accredited investors. However, these non-accredited investors must be sophisticated—meaning they possess sufficient financial or business experience to understand and evaluate the risks of the investment, either independently or with the assistance of a qualified purchaser representative. The sophistication requirement is qualitative, not formulaic, and imposes a higher diligence burden on the issuer when assessing the investor’s capacity.
A defining restriction under Rule 506(b) is the absolute prohibition on general solicitation and advertising. Issuers may not publicly promote the offering through media, internet posts, social platforms, or other broad channels. Communications must be targeted and selective, typically made to investors with whom the issuer or its agents have a pre-existing, substantive relationship. This prohibition reflects the traditional view of a “private placement” as a discreet negotiation between the issuer and known or personally referred investors. Violating this ban on general solicitation—even inadvertently—can disqualify the issuer from relying on the exemption and potentially trigger regulatory enforcement.
Because non-accredited investors are permitted under Rule 506(b), the SEC has imposed mandatory disclosure obligations when such investors participate. These disclosures must be equivalent in form and substance to those required in Regulation A offerings. Specifically, issuers are expected to provide:
- Detailed information about the company’s business, management, and operations;
- A description of the securities being offered and the associated risks;
- Financial statements covering the past two fiscal years, which must be audited if the issuer already has audited statements.
While accredited investors are not entitled to specific disclosures, the issuer must still avoid material misstatements or omissions under federal anti-fraud rules. In practice, this means most issuers provide all investors with a Private Placement Memorandum (PPM) or similar offering document. This serves not only as a disclosure tool but also as evidence of compliance if the transaction is ever scrutinized by regulators or challenged by investors.
All securities sold under Rule 506(b) are deemed “restricted securities” under Rule 144.
Rule 506(b) also includes a bad actor disqualification clause, borrowed from Rule 506(d). Issuers are therefore expected to conduct thorough diligence on all relevant parties and often require the completion of “bad actor questionnaires” to document compliance. A failure to do so can not only invalidate the exemption but expose the company to liability and potential rescission claims by investors.
To illustrate how our SaaS startup could rely on Rule 506(b), suppose that after its initial $2 million round under Rule 504, it plans a larger Series A financing round of $10 million. The company wishes to raise funds from several well-known VC firms (all accredited investors) and a handful of successful angel investors—two of whom do not technically qualify as accredited but are sophisticated and experienced in tech startup financing. The startup does not intend to advertise this offering publicly but instead reaches out to its existing investor network and personal referrals. This structure is ideal for Rule 506(b). To remain compliant, the company:
- Prepares and distributes a comprehensive PPM to all investors, even though disclosure is only mandatory for non-accredited participants.
- Verifies each non-accredited investor’s sophistication and, where needed, involves a purchaser representative.
- Obtains signed subscription agreements with investment intent representations and implements resale restrictions on all securities issued.
- Conducts internal diligence to ensure none of its directors, 20% owners, or advisors are subject to any “bad actor” events under Rule 506(d).
- Files Form D with the SEC within 15 calendar days after the first sale, thereby satisfying the federal notice requirement.
Through this structure, the SaaS startup avoids the burden of verifying accredited investor status required under Rule 506(c), gains flexibility to accept a small number of non-accredited but experienced backers, and preserves the private nature of the offering by avoiding public marketing.
Rule 506(c) – The General Solicitation Exemption
Rule 506(c) is the most recent addition to Regulation D, introduced by the SEC in response to the JOBS Act of 2012. It fundamentally transformed the landscape of private offerings by explicitly permitting general solicitation and advertising—a longstanding prohibition under traditional private placement doctrine. The rule gives issuers the power to publicly promote their offerings, provided that they meet certain rigorous requirements designed to preserve investor protection, particularly by limiting sales exclusively to accredited investors and requiring affirmative verification of that status.
Rule 506(c) allows companies of any size and maturity to raise an unlimited amount of capital from the public. There is no ceiling on the proceeds or number of purchasers, as long as each purchaser is an accredited investor and proper verification procedures are followed.
A defining feature of Rule 506(c) is its clear distinction between who may be offered securities and who may purchase them. The rule permits issuers to advertise broadly—through websites, email campaigns, social media, pitch events, crowdfunding platforms, and even television or radio—without the need for pre-existing investor relationships. This freedom, however, comes with a non-negotiable constraint: only accredited investors may purchase the securities. Moreover, it is not sufficient for investors to self-certify their accredited status; the issuer must take reasonable steps to verify that each investor truly qualifies under the accredited investor definition at the time of sale.
The verification obligation under Rule 506(c) is both substantive and distinct from Rule 506(b). In a 506(b) offering, it is enough for the issuer to form a reasonable belief based on information collected (such as an investor questionnaire) that the investor is accredited. In contrast, Rule 506(c) imposes a higher verification threshold: the issuer must use objective, documentary evidence or third-party confirmation to substantiate the investor’s status. Acceptable methods include reviewing tax returns or W-2s to confirm income levels, examining bank and brokerage statements to determine net worth, or obtaining letters from licensed attorneys, certified public accountants, or registered broker-dealers who have independently verified the investor’s accreditation.
The SEC has intentionally maintained a principles-based approach to verification. While it provides a non-exclusive list of acceptable methods, it does not mandate any one procedure. What qualifies as “reasonable steps” depends on the facts and circumstances of the offering—such as the nature of the solicitation, the risk of fraud, and the type of investors targeted. For example, if the issuer imposes a very high minimum investment amount (e.g., $1 million) and requires investors to certify that they are not financing the investment through debt, this may be sufficient in some contexts. In others, especially where public advertising reaches less sophisticated audiences, more rigorous steps may be required.
Notably, Rule 506(c) does not impose any specific disclosure requirements, regardless of whether investors are accredited. However, this absence of mandated disclosure does not immunize issuers from liability under anti-fraud provisions of federal securities laws. If material facts are misstated or omitted, investors have the right to bring claims under Section 12(a)(2) or Rule 10b-5. As a result, many issuers continue to prepare a Private Placement Memorandum or detailed offering deck, especially when raising funds from investors who are unfamiliar with the issuer or the industry.
Like the other provisions of Regulation D, securities sold under Rule 506(c) are treated as restricted securities. Investors may not resell these securities freely in public markets unless they meet the conditions of an applicable resale exemption. Issuers must ensure that investors understand these limitations and should incorporate restrictive legends, contractual resale restrictions, and stop-transfer instructions as part of their compliance protocol.
Rule 506(c) also incorporates the bad actor disqualification rules under Rule 506(d).
Turning again to our SaaS startup, suppose that after raising $10 million through Rule 506(b), the company wants to launch a follow-on round aimed at a much broader group of tech-savvy angel investors and fund managers across the U.S. To do this efficiently and reach a wider audience, the company decides to publicize the offering through a specialized startup financing platform and a curated investor newsletter with thousands of subscribers. This move makes Rule 506(b) unavailable due to the prohibition on solicitation. Instead, the company opts for Rule 506(c) and structures the offering accordingly.
To comply, the company:
- Advertises freely using digital marketing and webinars, while clearly stating that participation is limited to accredited investors.
- Engages its legal counsel and a third-party verification service to collect and review investor documentation, such as tax returns and balance sheet summaries.
- Applies a minimum investment threshold of $250,000 and requires each investor to certify that the investment is not financed through borrowed funds.
- Continues to issue a detailed PPM not because the rule requires it, but to manage risk, protect the company from future claims, and present a professional front to sophisticated backers.
- Reviews all relevant internal and external actors to ensure no disqualifying “bad actor” triggers exist that would jeopardize the exemption.
Through this approach, the SaaS company is able to conduct a high-visibility private offering—broadening its investor base and accelerating its capital raise—while remaining firmly within the regulatory contours of Rule 506(c).
Raising Capital Under Regulation D? We Help You Structure It Right
- Whether you're raising your first outside capital or planning a multi-million dollar round, we help you use Regulation D the way it was meant to be used: efficiently, compliantly, and strategically. From choosing between Rule 504, 506(b), or 506(c) to drafting investor documents and ensuring your offering avoids integration issues, we focus on getting the legal architecture right—so you can focus on growth
- We’ve supported founders, in-house counsel, and investor groups through complex private placements—drafting subscription agreements, verifying accredited investor status, managing disclosure obligations, and handling SEC Form D and state-level filings. If you're accepting even one non-accredited investor or planning general solicitation, we'll walk you through the tradeoffs clearly
- Because the rules are constantly evolving, we stay on top of SEC guidance and enforcement trends, from safe harbors under Rule 152 to the latest on bad actor disqualifications. You get a partner who understands how to balance regulatory risk with real-world fundraising pressure