Robert A. Mascioli

Robert Mascioli counsels entrepreneurs, family businesses and middle-market companies on a wide variety of business matters. Acting as their outside general counsel, Bob strives to learn the background, operations and strategies of his clients and seeks to align his legal advice with their goals to operate efficiently and effectively. He provides business and transactional representation to clients within industries such as technology and information technology, software and services, industrial services and distribution, venture capital/private equity, health care, and engineering and professional services.

Drawing on his past roles as an investment banker and the director of a university-based center for entrepreneurship, Bob has a diverse set of skills to help clients with mergers and acquisitions, angel, venture and private equity investments, board and shareholder relations, technology licensing, strategic partnerships and joint ventures, and business formation and structuring. Bob brings nearly 20 years of experience as a business and transactional attorney to his engagements.


In addition to general corporate representation, Bob’s experience in the technology and information technology industries includes handling investments by angel investors and venture/private equity firms, licensing agreements, employment agreements, service agreements, and mergers and acquisitions. His clients have included companies working in international logistics optimization, information technology services, and health care and biologics.

Select representation and representative transactions include:

  • An international logistics optimization company in connection with the purchase by two private equity firms of a significant minority preferred equity position ($60M) in the company.
  • A health care technology start-up company in a wide range of legal areas, including in connection with a research collaboration and subsequent license agreement with the animal health division of an international pharmaceutical company. 
  • An early-stage health care technology and biologics company in a wide range of legal areas, including general corporate representation, mergers and acquisitions, securities offerings, employment matters, and commercial litigation. Matters include:
    • A convertible note financing of $685,000, a Series A preferred equity financing of approximately $1.2M, a Series B preferred equity financing of approximately $2.6M and a convertible note financing of approximately $1.6M;
    • A secured lending facility and related biologics processing and commercialization agreement with a multi-national tissue recovery organization; and
    • The sale of a biologics product line to a medical distributor with a transaction value of $4M.
  • An entrepreneur in the sale of two IT services businesses (and general corporate matters) over a period of several years with an aggregate transaction value of over $4M.

Software and Services

Bob’s experience in the software and services industry includes handling licensing transactions, as well as offering counsel on structuring, forming and obtaining financing for start-up and early-stage companies. His clients have include software companies supporting the health care industry and higher education.

Select representative transactions include:

  • A privately-held online software and database company in a licensing transaction with two publicly-traded health care companies to build-out and host multiple web properties related to diet for chronically ill patients.
  • An entrepreneur in the growth and sale of a start-up financial aid and management software company and the subsequent structure, formation and angel round equity financing of an online marketplace for hobby enthusiasts.
  • A publicly-traded thin client software and hardware technology company in connection with various legal matters, including general corporate representation, mergers and acquisitions, and securities law.
  • A privately-held supply chain operating network in connection with various legal matters, including general corporate representation, customer agreements, and lending facilities.

Industrial Services and Distribution

Bob’s experience in industrial services and product distribution includes representing private and publicly-traded companies with general corporate matters, mergers and acquisitions, employment agreements, services agreements, and securities law issues and disclosure.

Select representative transactions include:

  • Leading and closing over 25 acquisition and disposition transactions with an aggregate value of over $200M for a publicly-traded industrial products/services sales and distribution company.
  • Representing an industrial service and materials company in connection with the construction (approximately $35M) and operation (approximately $5M annually) of three gypsum de-watering plants related to the “clean” production of electricity by a Mid-Atlantic utility company and the sale of synthetic gypsum resulting from such plants.
  • Representing a private equity firm in the acquisition of two industrial/commercial landscaping and winter services companies with an aggregate transaction value of $24M.
  • Represented a 30-plus person privately‑held engineering firm (specializing in wireless communications and civil engineering) in its sale to a private equity-backed, large regional full-service engineering firm (approximate value with earn-out between $8-9M).

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