Kim Lisa Taylor, Esq., is the founder and managing attorney of Syndication Attorneys, PLLC. She has guided entrepreneurs through hundreds of securities offerings totaling more than $5 billion. She is the author of two best-selling books on raising capital, How to Legally Raise Private Money and How to Raise Capital for Real Estate Legally, and hosts the Raise Capital Legally podcast and YouTube channel.
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Hiring a syndication attorney is one of the most consequential decisions in this business, yet at the point of hire, every option tends to look similar. PPMs appear alike from the outside, and most attorneys sound confident describing their experience, leaving little obvious signal to distinguish genuine expertise from a template-driven practice. Five specific questions offer a real evaluation framework for this decision, applicable to any attorney under consideration.
Table of Contents
Why the Point of Hire Is the Hardest Place to Evaluate
Confidence during an interview does not reliably indicate depth of experience, and the outward similarity of offering documents makes it difficult to judge quality before an engagement begins. A structured set of questions, asked consistently across every attorney under consideration, provides a more reliable basis for comparison than general impressions.
How Many Reg D Offerings Have You Drafted in the Last 12 Months?
The more useful question is not how many years an attorney has practiced, but how many offerings were drafted in the past year specifically. A meaningful answer includes a specific number along with detail about the types of deals involved, whether 506(b), 506(c), funds, or syndicates, since deal volume builds the pattern recognition needed to anticipate edge cases, structural problems, and filing deadlines.
Those deal types carry very different conditions. Under the SEC's guidance on Rule 506(b), an offering cannot use general solicitation and may include no more than 35 non-accredited investors in any 90-day period, while Rule 506(c) permits general solicitation only if every purchaser is accredited and the issuer takes reasonable steps to verify that status. An attorney drafting both regularly will know where each one tends to break down.
An attorney who redirects the conversation toward total years in practice rather than recent volume is worth noting, since recency matters given how frequently the regulatory environment shifts. The SEC's 2020 amendments to the exempt offering framework, described in its press release SEC Harmonizes and Improves "Patchwork" Exempt Offering Framework, are one example of rules changing beneath established practices. An attorney who completed ten offerings in the last 12 months is generally more current than one who completed ten offerings spread across the last decade.
Do You Represent Syndicators, Investors, or Both?
A firm that also represents real estate investors, meaning individuals who invest in syndication deals, creates a structural tension between protecting a sponsor client and maintaining investor client relationships. The strongest answer to this question is unambiguous: sponsors only, with no investor clients in the same asset class, so the conflict never arises in the first place.
An answer suggesting the firm represents both sides while managing conflicts appropriately warrants closer scrutiny, since a securities engagement benefits most from a structure where the potential conflict simply does not exist rather than one that must be actively managed.
What Is Your Process for Deal Structuring Before Documents?
Offering documents reflect decisions that should already be finalized, including the choice between 506(b) and 506(c), fund versus syndicate structure, entity design, and waterfall mechanics. An attorney whose process begins with a questionnaire followed immediately by drafting is effectively working backwards from the structure rather than designing it deliberately.
The exemption choice alone shapes how a sponsor can market the deal. The SEC states that a Rule 506(b) offering may not use general solicitation or advertising, and if non-accredited investors participate, the issuer must provide them with disclosure documents and financial statement information specified in Rule 506. A sponsor who plans to advertise, or who expects non-accredited investors, needs that decision made before a single document is drafted.
The preferable process involves a structured conversation about the deal's goals, investor base, timeline, equity split, and distribution approach before any document drafting begins, ensuring the structure is designed first and the documents implement that structure afterward. Syndication Attorneys addresses this through its Pre-Offering Program and its work on deal structures, waterfalls, and management fees. Where an attorney describes sending a questionnaire and proceeding directly to drafting, it is worth asking what happens in between; the absence of a clear answer suggests limited structuring work is actually occurring.
How Do You Handle Blue Sky Filings?
This question distinguishes attorneys who treat Blue Sky filings as core to the engagement from those who treat them as an afterthought. Blue Sky notice filings are required in every state where an investor is accepted, separate from the federal Form D, typically due within 15 days of the first sale in that state, with a distinct form and fee per state.
The SEC confirms that although Rule 506 offerings receive federal preemption from state registration and qualification, the states still have authority to require notice filings and collect state fees, as stated in its guidance on Rule 506(b) and Rule 506(c). The federal Form D is a separate obligation, due within 15 days after the first sale under the SEC's guide to filing a Form D notice, and filing it does not satisfy any state requirement.
A strong answer confirms that these filings are included in the engagement, that investor states are tracked as the raise progresses, and that confirmation documentation is provided for every state. Syndication Attorneys' Regulation D offering packages include Form D and Blue Sky filings for this reason. A vague response, such as suggesting the filings can be added if needed or are usually handled separately, should prompt a request for these filings to be named as an explicit item, rather than assumed as a default inclusion, in the engagement letter.
Have Your Documents Ever Been Reviewed in Litigation or a Regulatory Inquiry?
This question is deliberately uncomfortable, since documents that have been tested in an adversarial setting reveal something meaningful, whether they held up under scrutiny or were found deficient in a way that changed how the firm drafts going forward. Any attorney with sufficient experience in this practice area will likely have clients who encountered disputes at some point, and the more relevant question is how the documents performed when tested.
The stakes are real even in an exempt offering. The SEC's Frequently Asked Questions About Exempt Offerings explains that all securities transactions, exempt or not, are subject to the federal antifraud provisions, that the government enforces them through criminal, civil, and administrative proceedings, and that private parties can also sue. If the exemption's conditions are not met, purchasers may be able to return their securities and recover their purchase price.
A transparent answer acknowledges past disputes and describes how the documents held up in those situations. A defensive response, or a claim of no awareness of any such history, may indicate either limited exposure to these edge cases or a lack of tracking regarding how the firm's own work performs under pressure.
Applying This Framework to Any Attorney
The first two questions, covering deal volume and representation conflicts, tend to receive reasonably strong answers from most attorneys in this space, since these are well-understood considerations. The remaining three questions, covering deal structuring process, Blue Sky filing handling, and litigation history, tend to reveal the most meaningful differences between firms, since they require specificity that is harder to provide without direct, relevant experience. Vague responses to any of these specific questions are themselves informative, and this same framework applies equally when evaluating Syndication Attorneys.
Frequently Asked Questions
What is the difference between a Rule 506(b) and a Rule 506(c) offering?
A Rule 506(b) offering prohibits general solicitation and may include up to 35 non-accredited investors in any 90-day period. A Rule 506(c) offering permits general solicitation, but every purchaser must be accredited and the issuer must take reasonable steps to verify that status.
Does filing a Form D satisfy state Blue Sky requirements?
No. The SEC states that a company selling securities must comply with both federal rules and the securities laws of the states where securities are offered and sold, and that states may impose their own notice filing requirements and fees, according to its exempt offerings FAQ.
When is the federal Form D due?
Within 15 days after the first sale of securities in the offering. The SEC defines the date of first sale as the date the first investor is irrevocably contractually committed to invest, and it charges no fee for a Form D notice or amendment, per its guide to filing a Form D notice.
Do antifraud rules apply if my offering is exempt from registration?
Yes. The SEC confirms that all securities transactions, even exempt ones, are subject to the federal antifraud provisions, and the company is responsible for false or misleading statements made on its behalf, whether oral or written.
What should an engagement letter say about Blue Sky filings?
It should name Blue Sky notice filings as an explicit line item, covering every state where investors reside, with investor states tracked during the raise and confirmation documentation provided for each state.
Conclusion
Sponsors who want to apply this evaluation framework directly may schedule a consultation at syndicationattorneys.com/schedule to review their specific deal structure and current documentation needs.
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This content provides general information on federal securities law and is directed to non‑Florida residents or companies. It is not legal advice and is not intended as advertising or solicitation of legal services for Florida residents or Florida law matters. Use of this content or contacting us about it does not create an attorney–client relationship.
