These alternatives include crowdfunding, angel investment, revenue-based financing, invoice factoring, and preferred equity. Traditional bank lending has become more restrictive due to evolving regulatory requirements and risk management standards.

Limitations of Traditional Bank Financing

• Increased regulatory and capital reserve requirements: Following the 2007–2008 financial crisis, the Basel III framework strengthened capital reserve requirements, reduced allowable leverage, and increased liquidity standards for banks. This has resulted in stricter lending criteria and reduced access to credit for higher-risk borrowers.

• Rigid underwriting and loan covenants: Loan agreements often require companies to maintain specific financial ratios, such as EBITDA thresholds, limiting operational flexibility.

• Cash flow and collateral restrictions: Banks typically favor asset-based or cash flow-based lending, which can disadvantage high-growth or technology companies with limited tangible assets.

• Need for flexible financial instruments: Private lenders and investment funds offer more tailored financing structures, including hybrid instruments that combine elements of debt and equity, often with more flexible repayment terms.

Preferred Equity as a Financing Alternative

Among alternative financing methods, preferred equity has gained popularity because it can provide capital without the constraints of traditional debt financing. However, it also introduces unique legal and financial risks that must be carefully evaluated.

Key Risks of Preferred Equity

• Subordination and priority: Preferred equity ranks below both secured and unsecured debt, meaning those creditors must be paid first in the event of default.

• Lack of creditor remedies: Preferred shareholders are not creditors and therefore cannot foreclose on assets. Remedies are typically limited to negotiated rights such as increased returns or voting power.

• No mandatory bankruptcy protections: In bankruptcy, preferred equity holders are treated as equity investors and do not have the same enforcement rights as creditors.

• “Legally available funds” requirement: Redemption or buyout rights depend on the company having legally available funds, as determined by the board of directors.

• Structural risks and dilution: Preferred equity may be diluted or subordinated if additional debt or equity is issued without proper protections in place.

• Tax and phantom income risk: Investors may incur taxable income on accrued returns that have not been paid in cash.

• Illiquidity: Investments are typically locked in until a defined exit event, such as a sale or refinancing.

Choosing the Right Financing Strategy

Selecting the appropriate financing structure requires careful evaluation of both immediate capital needs and long-term implications. Business owners and boards of directors must understand the trade-offs associated with each option and take steps to mitigate potential risks.

The attorneys at Corporate Securities Legal LLP provide guidance on structuring financing solutions that align with business objectives while protecting against legal and financial exposure.

Illegal insider trading can expose a company and its leadership to severe legal, financial, and reputational consequences. A well-structured insider trading policy helps protect the company by establishing clear expectations and discouraging improper conduct.

The SEC has published guidance outlining best practices for companies developing insider trading policies.

Who and What Is Covered

An insider trading policy should clearly identify who is subject to the rules and what types of activities are restricted. SEC Rule 10b-5 prohibits corporate insiders from using confidential corporate information to trade securities for personal gain.

Covered individuals may include:

• Corporate officers and directors;
• Employees with access to sensitive information;
• Consultants and contractors;
• Significant shareholders;
• Family members and household residents of insiders.

The rule also prohibits “tipping,” which occurs when insiders share confidential information with third parties who then use that information to trade securities.

A company’s policy should summarize relevant federal securities laws—including the Securities Exchange Act of 1934 and SEC Rule 10b-5—and explain how insiders may trade securities while remaining compliant with these regulations.

Defining Key Terms

Clear definitions help employees understand what information and conduct may create insider trading risks. Important terms typically addressed in the policy include:

Material Information: Information that could reasonably affect the value of the company’s securities or influence an investor’s decision to buy, sell, or hold stock. Examples include:

• Financial projections;
• Proposed mergers or acquisitions;
• Significant new products or services;
• Major corporate transactions.

Non-Public Information: Information that has not yet been widely disseminated to the public or fully absorbed by the market.

Insider: Any individual who has access to material non-public information due to their relationship with the company, including officers, directors, large shareholders, and individuals who receive confidential tips.

Trading Restrictions and Procedures

An insider trading policy should establish clear rules governing when and how insiders may trade company securities.

Common procedures include:

Blackout Periods: Pre-determined periods during which certain executives and directors may not trade securities, such as around quarterly earnings announcements or other major corporate events.

Event-Specific Trading Restrictions: Temporary restrictions imposed when the company is involved in confidential transactions such as merger negotiations or strategic business developments.

Pre-Clearance Requirements: Directors, officers, and employees with access to confidential information may be required to obtain approval from a designated compliance officer before trading company securities.

Compliance, Enforcement, and Penalties

An effective insider trading policy must address enforcement mechanisms and the consequences of violations.

Key components include:

Designated Compliance Officer: A specific individual—often the company’s general counsel—responsible for administering the policy and answering compliance questions.

Reporting Violations: A confidential reporting channel allowing employees to report suspected violations without fear of retaliation.

Penalties: Violations may result in serious consequences, including:

• Disciplinary action or termination of employment;
• Civil enforcement actions by regulatory authorities;
• Criminal prosecution and imprisonment.

Insider trading penalties can be severe and may include:

• Up to 20 years imprisonment;
• Criminal fines of up to $5 million;
• Civil penalties of up to three times the profits gained or losses avoided.

Implementation and Best Practices

For an insider trading policy to be effective, it must be properly implemented and communicated throughout the organization.

Best practices include:

• Legal Review: Have the policy drafted or reviewed by experienced securities counsel.
• Employee Training: Conduct regular training sessions for employees, especially those with access to sensitive information.
• Monitoring Systems: Track trading activity to detect unusual or suspicious patterns.
• Clear Communication: Provide employees with electronic access to the policy and distribute written copies to directors and senior management.
• Regular Updates: Revise the policy as the company grows or transitions from a private company to a publicly traded entity.

Why Legal Guidance Matters

As companies grow and evolve, insider trading risks and compliance requirements may also change. Maintaining a clear and enforceable insider trading policy helps protect the company and its leadership from significant legal exposure.

The attorneys at Corporate Securities Legal LLP assist companies in developing insider trading policies, implementing compliance programs, and navigating federal securities regulations.

Contact Corporate Securities Legal LLP to ensure your company’s insider trading policies remain compliant with current securities laws and regulatory expectations.

When starting a business, advance planning can significantly reduce tax liability when the time comes to sell the company—whether through retirement, acquisition, or other liquidity events. The Qualified Small Business Stock (QSBS) exemption, authorized under Internal Revenue Code Section 1202 and enhanced by recent legislation, allows eligible business owners to exclude substantial capital gains realized upon the sale of their company stock.

For qualifying stock, business owners may exclude up to $15 million in gain above their tax basis when the business is sold, creating powerful long-term tax advantages for founders and early investors.

Key Benefits of the QSBS Exemption

The enhanced QSBS benefits apply only to stock purchased on or after July 4, 2025, and provide several important advantages.

Increased Exclusion Limits
Eligible shareholders may now claim up to:

• $15 million gain exclusion for qualifying stock acquisitions;
• An increase from the prior $10 million exclusion applicable to earlier stock purchases.

Reduced Holding Periods with Partial Benefits
The revised rules allow partial exclusions based on holding duration:

• 50% exclusion for stock held 3–4 years;
• 75% exclusion for stock held 4–5 years;
• 100% exclusion for stock held 5 years or longer.

Previously, shareholders were required to hold stock for at least five years to receive any exclusion benefit.

Higher Gross Asset Threshold
The qualifying company asset limitation has increased:

• From $50 million to $75 million in gross assets;
• Asset valuation is based on tax basis, not fair market value.

These benefits apply only to newly issued stock and do not apply to shares obtained through stock conversions or exchanges.

Company Eligibility Requirements

To qualify for QSBS treatment, a company must meet several structural requirements:

• The business must be organized as a C-Corporation;
• The entity must be organized and registered within the United States;
• Stock must be purchased directly from the corporation using money, property, or services;
• Purchases from existing shareholders do not qualify.

Entities such as LLCs, partnerships, and S-corporations are not eligible for QSBS treatment.

Active Business Requirement

The corporation must operate an active trade or business using at least 80% of its assets in operational activities. Passive investment companies do not qualify, although reasonable working capital reserves and research and development activities are permitted.

Certain industries are specifically excluded, including:

• Professional service firms (law, medicine, accounting);
• Banking, insurance, and financial services businesses;
• Farming and natural resource extraction companies;
• Hospitality businesses such as hotels and restaurants;
• Businesses primarily dependent on employee reputation or personal skill.

Calculating the QSBS Exclusion

Determining the available tax exclusion requires applying two limitations in a specific order.

Dollar Limitation
The maximum exclusion depends on the acquisition date:

• $10 million for stock acquired before July 4, 2025;
• $15 million for stock acquired on or after July 4, 2025.

Alternatively, shareholders may exclude gains equal to ten times their stock basis, recalculated annually—often benefiting founders contributing appreciated property.

Percentage Limitation
After applying the dollar limitation, the allowable exclusion percentage is determined based on holding period requirements.

When exclusions are less than 100%:

• Non-excluded gains are subject to a special 28% federal capital gains tax rate;
• Gains exceeding dollar limitations are taxed at standard capital gains rates.

Strategic Planning Opportunities

Proper planning can substantially increase QSBS benefits. Effective strategies may include:

• Timing and structuring stock issuances;
• Property contribution planning;
• Multi-entity ownership structures;
• Integration with family and estate planning objectives.

Early legal and tax planning ensures eligibility requirements are preserved long before a liquidity event occurs.

The securities lawyers at Corporate Securities Legal LLP advise founders, investors, and growing companies on structuring businesses to maximize QSBS eligibility and long-term tax efficiency.

Contact Corporate Securities Legal LLP to schedule a consultation and learn how advance planning can help you capture the full benefits of the QSBS tax exemption.

How is the definition of an accredited investor being expanded?

The proposed rule will amend the definition of an “accredited investor” as follows:

With regard to individuals, the proposed rule would add the term “spousal equivalent” to the definition of a spouse, and give accredited investor status to individuals:

• that have certain professional certifications or designations or other credentials; or
• whose status as a private fund’s “knowledgeable employee.”

With regard to entities, the proposed rule would expand the list of entities, including, but not limited to:

• entities that meet an investments test; and
• family offices with at least $5,000,000 in assets under management and their family clients.

Background

Under the U.S. federal securities laws, a company that offers or sells its securities must register the securities with the Securities and Exchange Commission (“SEC”) or qualify for an exemption from registration.[1] Regulation A+ and crowdfunding provide an exemption from registration that allow the company to raise capital to with unaccredited investors, however, the process for preparing these offering documents can oftentimes be just as burdensome on the company as registering the securities. Rule 506 of Regulation D provides additional exemptions from registration; for these exemptions, we recommend only raising capital from accredited investors. If the SEC is successful in broadening the scope of who is considered to be an accredited investor, more investors will hold accredited investor status, making it easier for private companies trying to raise capital using Rule 506.

What is an accredited investor?

Rule 501 of Regulation D of the Securities Act of 1933 (the “Securities Act”) defines an accredited investor. In summary, an accredited investor is: an individual that has a net worth of $1,000,000, excluding their primary residence; or an individual that has an annual income of $200,000 or more (or $300,000 combines with their spouse) for two years and has a reasonable expectation of meeting those income requirements in the upcoming year. Additionally, Rule 501 defines specific types of entities; and directors, executive officers, or general partners of the issuing company as being accredited.

Public Policy

The SEC depicts the “accredited investor” definition as a central component of Regulation D, stating that it is “intended to encompass those persons whose financial sophistication and ability to sustain the risk of loss of investment or ability to fend for themselves render the protections of the Securities Act’s registration process unnecessary.”[2] Considering this definition, it’s clear why the SEC would like to expand the definition of an accredited investor to “identify more effectively institutional and individual investors that have the knowledge and expertise to participate in our private capital markets and therefore do not need the additional protections of the registration under the Securities Act.”[3]

Wilson Bradshaw LLP is a boutique securities law firm in Irvine, California and New York City. We help businesses solicit investors for both public and private companies in a compliant manner. We restrict our practice to securities law, focusing on private and public offerings and SEC enforcement work.

[1] U.S. Securities and Exchange Commission, Accredited Investor, Fast Answers (Nov. 27, 2017), https://www.sec.gov/fast-answers/answers-accredhtm.html.

[2] U.S. Securities and Exchange Commission, Report on the Review of the Definition of “Accredited Investor”, Files (Dec. 18, 2015), https://www.sec.gov/files/review-definition-of-accredited-investor-12-18-2015.pdf.

[3] U.S. Securities and Exchange Commission, 17CFR Parts 230 and 240, Release Nos. 33-10734; 34-87784; File No. S7-25-169, Amending the “Accredited Investor” Definition (Dec. 18, 2019), https://www.sec.gov/files/review-definition-of-accredited-investor-12-18-2015.pdf.

How to Comply with Rule 144 as a Non-Affiliate

What is Rule 144?

Rule 144 under the Securities Act of 1933 is enforced by the Securities and Exchange Commission (“SEC”). When a shareholder acquires restricted securities or holds control securities, the shareholder must find an exemption from the SEC’s registration requirements in order to sell the securities in a public marketplace. One exemption is found under Section 4(a)(1), allowing shareholders to sell restricted or control securities in a public sale when specific conditions laid out in Rule 144 are met.

The specific conditions that must be met to rely on Rule 144 depend on whether or not the holder is an affiliate; this depends on the control that the individual/company has on the issuer company. Typically, affiliates are officers, directors, and 10% shareholders. Their shares are called “Control Securities” and have restrictions placed in them when sold to non-affiliates.

How do shareholders acquire restricted securities?

Shareholders often acquire restricted securities in two ways:

1. Private placement offerings, Regulation D offerings, or employee stock option plans, as compensation for services rendered or in exchange for providing start-up capital to the Company.[1] These are unregistered, private transactions that restrict stock from being sold in the public marketplace.
2. The shareholder buys securities from a controlling person or affiliate. Even if the securities were not restricted in the affiliate’s hands, they become restricted through the sale because they are control securities.

When securities are restricted, a restrictive legend is usually stamped on the back of the stock certificate, prohibiting its sale in the public marketplace unless they are registered with the SEC or are exempt from the registration. When a buyer acquires control securities, the stock certificate is not usually stamped with a restrictive legend but the restrictions still apply.

Rule 144 Non-Affiliate Conditions

For a non-affiliate to sell their restricted stock on the public marketplace using Rule 144, they must meet these conditions:

1. The shareholder must satisfy the holding period by holding the shares for a certain period of time.[2] If the company is a “reporting company” and is subject to the reporting requirements of the Securities Exchange Act of 1934, then the seller must hold the securities for at least six months. If the company is not subject to reporting requirements, then the shares must be held for at least one year.
   • Tacking can help a non-affiliate shareholder satisfy the holding period. If an individual or entity purchases restricted securities from another non-affiliate, the shareholder can tack on their holding period to the non-affiliate’s holding period.
2. There is adequate current information about the company publicly available. For reporting companies, this means compliance with the periodic reporting requirements of the Exchange Act.[3] For non-reporting companies this means that company information is publicly available, including information regarding the nature of its business, the identity of its officers and directors, and its financial statements.[4]

Rule 144 can be used to sell restricted or control securities of the company in the public marketplace, provided certain conditions are met. If you’re an affiliate within the meaning of Rule 144, then you will be subject to additional requirements. Oftentimes the company’s transfer agent will require a Rule 144 legal opinion letter stating that these requirements have been satisfied before the restrictive legends can be removed.

Wilson Bradshaw LLP is a boutique securities law firm in Irvine, California and New York City. We help individuals remove the restrictive legends on the back of their stock certificates in order to sell the securities in the public marketplace by providing Rule 144 legal opinions. We restrict our practice to securities law, focusing on private and public offerings and SEC enforcement work.

[1] Rule 144(a)(3).

[2] Rule 144(d).

[3] Rule 144(c)(1).

[4] Rule 144(c)(2).