James A. Wolff

Representative Experience

• Built and lead counsel for a $240 million strategic client portfolio spanning over thirty emerging technology companies, guiding them through complex capital raises, governance structuring, and regulatory compliance initiatives.
• Lead transactional counsel for multi-million-dollar financings, including a $50 million Series A Regulation D private placement and a $1 million warrant issuance for a dual-use aerospace company, each involving sophisticated structuring, investor negotiations, and cross-border considerations.
• Served as general counsel to venture-backed and IP-intensive startups across sectors including AI, medtech, fintech, and modular architecture, delivering full-stack legal infrastructure from formation through capital deployment and IP capture.
• Authored and negotiated enterprise-grade commercial agreements, including an AI deployment services agreement with a national real estate platform founded by former MetLife and E*TRADE executives, successfully managing over 30 rounds of redlines and phased service deliverables.
• Architected and implemented capital stack restructuring across multiple corporate conversions, including LLC-to-C-Corp restructures, dual-entity operating models, and founder-led recapitalizations to support future rounds and preserve control.
• Advanced securities counsel for Regulation D, CF, and A+ offerings, delivering investor compliance frameworks, tailored SAFE and RSPA instruments, and supporting Blue Sky filings and EDGAR submissions.
• Drafted multi-jurisdictional and cross-functional IP and contractor frameworks, including standalone assignment agreements, generative AI ownership clauses, and founder vesting mechanisms designed for defensible growth.
• Led corporate cleanup and governance audits for high-growth companies onboarding to cap table platforms such as Equity Shift, advising on capitalization table reconciliation, board ratifications, and securities compliance readiness.
• Provided regulatory and strategic advisory on digital asset and AI compliance, including stablecoin integration under GENIUS Act frameworks and commercialization strategy for AI-augmented IP portfolios.
• Supported asset protection and estate planning strategies, including real estate-to-LLC transfers aligned with intergenerational planning, trust compliance, and S-election governance preservation.
• Retained and represented Silicon Valley venture capital and investment relations agency for their incorporation and corporate governance activities.
• Retained and represented interior architecture firm for production of vendor contracting agreements.
• Drafted loan agreement for $50 million dollar conditional-recourse financing tranche for startup fintech company with multiple customized clauses reflecting negotiated terms.
• Retained and represented multi-million-dollar fintech startup for fractional general counsel services.
• Negotiated and drafted bilateral Non-Disclosure Agreement for negotiations related to a $180 million dollar transaction in an ongoing public-listed company reverse merger negotiation.
• Negotiated and drafted a Letter of Intent for a $15 million dollar acquisition as part of a long-term roll-up strategy by a technology business client.
• Negotiated and drafted Chief Operating Officer Agreement for software technology business client and drafted amended and restated corporate bylaws and employee policy manual including requisite Board and Stockholder written consent authorizations.
• Drafted exit agreement in business partnership dispute and negotiated and drafted general surrender and release agreement.
• Represented Fortune 50 Company in insurance defense litigation and related complex-commercial litigation.
• Performed a due diligence review and conducted corporate governance operations including board resolutions, special stockholder meetings, and amended certificates of incorporation for a technology company closing on a $50 million dollar loan agreement for a biotech startup.
• Retained and represented a multi-million-dollar startup in ongoing Delaware Federal court complex commercial litigation.
• Negotiated and drafted a Master Services Agreement for a U.S.-International manufacturing and operations contract related to the deployment of proprietary water-filtration technology by a technology company.
• Represented Silicon Valley Investor Relations and Go-To-Market agency involved in early-stage Seed and Series A level emerging technologies companies overseeing formation, corporate governance, and compliance operations.
• Representation of client (Seller) of a real estate investment company in the creation of a multi-party JV agreement for the purchase of residential property, construction renovations, and contemplated market placements; negotiated key terms including equity allocations and conducted due diligence formation of requests and related analysis.
• Representation of client (Seller) of a paper supply and delivery company in the acquisition by buyer as part of buyer’s roll-up strategy; negotiated agreement key terms, assisted in valuation analysis and earn-out terms, and managed due diligence campaign including request lists and responses.
• Representation of client (Seller) of a restaurant and nightlife business in drafting and negotiating Stock Purchase Agreement, formulating reps and warranties, conducting due diligence requests and responses, liquor license application review, seller’s resolution, and drafting and filing Amended Certificate of Incorporation with Preferred Stock tranche adjusting equity allocation.
• Representation of client (Seller) in Asset Purchase Agreement sale for nightclub establishment (Buyer), drafted and negotiated key terms, drafted liquor license corporate change of ownership application, drafted Bill of Sale, reps and warranties, restrictive covenants, bulk sales notice, closing checklists, confession of judgment, escrow agreements, re-assignment of lease, indemnification agreements for buyer and seller, promissory note guaranty, general security agreement boilerplate, seller’s resolution, buyer’s resolution, UCC1 filing and schedule, and stock pledge and escrow agreement.
• Representation of investment bank board of directors in partnership dispute issue relating to c-suite executive termination and compensation package payout dispute.
• Representation of an architect-seller (Buyer) in the negotiation of a Stock Purchase Agreement; negotiated key terms and secured a price of $1.9 million, drafted custom rep and warranties covenants, drafted associated promissory note guaranty and renegotiated related employment agreement terms and covenants.
• Representation of brick-and-mortar accounting firm (Seller) in two post-Asset Sale Agreement business disputes in American Arbitration Association and associated Supreme Court litigation proceedings, renegotiated business purchase price terms, and drafted and negotiated settlement agreement with payment schedules.
• Representation of an Asset Management company Chief Information Officer and Board Director (Buyer) as outside counsel for its corporate due diligence review as part of a renegotiation of equity and profit allocations, and prepared legal memorandum with recommended changes to its corporate governance documentation in support of client’s proposed restructuring.
• Representation of client (Buyer) in its investment into a Professional Employer Organization entity (PEO)(Seller), negotiated Unit Purchase Agreement key terms, conducted reps and warranties due diligence, analyzed material risk disclosures statements, and analyzed its amended and restated operating agreement.
• Secured a $2.5 million arbitration award in a dispute regarding a New York diamond dealer’s breach of business sale contract.
• Settled commercial tenant insurance policy lawsuit relating to premises liability issues in the post-pleadings and post-discovery stage; negotiated a premium settlement for the client above expectations and resolved five years of ongoing litigation.
• Negotiated the settlement of an insurance claim related to alleged employee negligence.
• Resolved construction litigation related to subcontractor schedule and fixture characterization and damages liability; resolved pre-trial following depositions exposing subcontractor weaknesses.

Professional and Community Involvement

• United Nations Association, Southern District of New York, Executive Board Member
• National Space Society, Board of Directors: Policy Leadership Team: Advocacy Manager
• Space Court Foundation, Director of Development
• New York City Bar Association
  • Emerging Technologies and Venture Capital Committee
  • Aerospace and Space Law Committee
  • Corporation Law Committee
• New York State Bar Association, Member

• Martindale-Hubbell Gold Client Champion, 2017-2024
• Super Lawyers magazine, “New York Metro: Rising Stars,” Business and Corporate Award, 2021-2024
• American Registry, Client Champion Award, 2018-2023
• American Registry, “America’s Most Honored Lawyers Award,” 2024
• NASA, “Entrepreneur’s Challenge Award,” 2023

• Author, “Mastering Business Dynamics: Entrepreneurial Leadership & Strategy: From Vision to Execution: Navigating the Complex World of Enterprise Success,” 2024