Winterfell Investments, LLC

Data-Driven,
Thematic Investing.

Winterfell Investments is a thematic, data-driven independent sponsor that aligns closely with investors capital providers. Our approach is grounded in quantitative analysis, repeatable processes, and a conviction that the most durable returns come from building operational excellence into fragmented markets.

Meet the Team

Managing Partner

Leigh Lommen

Leigh Lommen helped his brother and father’s business grow from under $50M in revenues to over $200M in revenues, while they made 23 acquisitions and integrated successfully within a franchisee environment.

Leigh has been a professional options trader on the floor of the CBOE and CME and has extensive experience in private investments.

Undergraduate: Finance and Investment Banking, University of Wisconsin – Madison

Masters in Science: Financial Mathematics, University of Minnesota – Twin Cities

MBA: Columbia University

M&A Analyst Intern

Bennett Barron

Bennett Barron was born and raised in Dallas, TX and graduated from Jesuit College Preparatory School of Dallas. He is a rising sophomore attending the University of Alabama on a full ride scholarship, majoring in Finance and Economics with a minor in Biology. Through his internship with Winterfell, he has gained valuable experience in valuation and business strategy across a variety of industries. In his free time, Bennett enjoys a round of golf, grilling, and playing guitar & piano..

Managing Partner

Gustavo Silva

Gustavo Castro e Silva is a Partner at Winterfell, where he focuses on growth capital, structured credit, leveraged finance, and value creation. He has more than fifteen years of experience in private capital markets spanning infrastructure, technology, financial services, and consumer sectors.

Before joining Winterfell, Mr. Castro e Silva held senior roles at Arsenal Capital Partners, Guggenheim Partners, Invepar Group, CVC Credit Partners, and BNDES, Brazil’s national development bank.

M.S. from MIT Sloan School of Management and a J.D./LLM from Northwestern University Pritzker

School of Law

Law Degree from IBMEC in Brazil

Investment Criteria

Winterfell Investments utilizes data-driven investment theses to source and partner with family-owned and operated businesses with the intent of standardizing processes and building out management with an eye toward organic growth and acquisitive growth. Winterfell invests in companies as small as $1M in EBITDA to $20M in EBITDA.

To learn more about Lower Middle Market Investment Criteria

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