Navigating the Independent Sponsor Landscape: A Conversation with Robert Connolly, Levenfeld Pearlstein

[Published on November 21st 2025]

In this video interview we speak with Robert Connolly, the leader of the independent sponsor and private equity practice at Levenfeld Pearlstein, a prominent law firm based in Chicago. With over 15 years of experience working with independent sponsors, Robert shares valuable insights into the evolving landscape of the independent sponsor market.

Discover how the growth of independent sponsors is creating new opportunities in the lower middle market, especially as traditional private equity firms grapple with older investments. Robert discusses the importance of structuring deals effectively, including key considerations at the letter of intent stage, tax implications, and the significance of qualified small business stock.

Learn what makes a well-structured independent sponsor deal, focusing on the balance of risk, reward, and alignment among sponsors, investors, and sellers. Robert also offers practical advice for new independent sponsors, emphasizing the importance of performance, process, and people in building successful partnerships.

 

In this video:

00:00:00 - Introduction to Independent Sponsorship
00:00:15 - Growth of the Independent Sponsor Market
00:00:37 - Opportunities for Capital Providers and Sponsors
00:01:31 - Value Creation for Sellers
00:02:12 - Common Structuring Mistakes
00:03:41 - Importance of Early Planning
00:04:13 - Key Elements of a Well-Structured Deal
00:05:30 - Advice for New Independent Sponsors
00:06:30 - Focus on Performance, Process, and People
00:07:24 - The Importance of Networking and Relationships
00:08:19 - Conclusion and Invitation to Connect

About the Author
Rob is a Partner in LP's Corporate Practice Group. He leads Levenfeld Pearlstein’s Independent Sponsor team, co-leads its Private Equity team, and previously served as the Corporate Practice Group Leader. His practice focuses on M&A, private equity, and corporate transactions in the middle market and lower middle market across multiple industries throughout the United States. He has extensive experience leading a wide spectrum of complex transactions, including mergers and acquisitions, divestitures, minority investments, joint ventures, recapitalizations, restructurings, securities offerings, and other business transactions. Rob takes a client-centric approach and combines his deep transaction experience, legal knowledge, and business acumen to focus on the issues that matter to help his clients achieve successful outcomes that align with their business, risk tolerance, and objectives. Rob has been recognized in mergers and acquisitions and corporate law by the Legal 500, Super Lawyers and Leading Lawyers.

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