Sterling is a corporate attorney who guides clients through both major transactions and day-to-day business matters. Private equity firms, private companies, family offices, strategic buyers, venture capital firms, and independent sponsors call on him for advice as they navigate complex decisions. Investors and entrepreneurs also seek his strategic guidance as they invest in new ventures or build new businesses.

In his transactional practice, Sterling negotiates and structures lower middle-market and middle-market mergers, acquisitions, joint ventures, management buyouts, and private placements. He leads due diligence reviews, drafts core documents, and negotiates agreements for both buy-side and sell-side deals. Whether he is representing a large private equity firm, a venture capitalist, or an independent sponsor building its reputation, he commits to understanding his client’s priorities and driving the full life cycle of the transaction with his client’s goals in mind.

Sterling also acts as outside general counsel for clients, serving as a trusted advisor who utilizes effective strategies to manage risk. His experience structuring matters, operations, corporate governance, and more positions him as a valuable resource for entrepreneurs and investors building their businesses and portfolios. Sterling leverages his colleagues’ diverse skillsets to provide legal counsel in other areas, such as commercial lending, real estate, intellectual property, litigation and dispute resolution, labor and employment, employee benefits, and bankruptcy and restructuring.

A born-and-raised Chicagoan with four degrees from Northwestern University, Sterling is an active alumnus who is ingrained in the community. In his undergraduate tenure, he served as captain of the university’s men’s varsity basketball team. His passion for athletics inspired him to develop a sports law practice focused on contract negotiations.