INVESTOR • ENTREPRENEUR • PRIVATE CREDIT EXECUTIVE
Leonard (Len) Tannenbaum, CFA
Leonard “Len” Tannenbaum, CFA is an investor, entrepreneur, and private credit executive with over three decades of experience investing in credit and building investment businesses.
He is the founder of Tannenbaum Capital Group and previously founded Fifth Street, which grew into a national alternative credit platform serving middle-market companies.
Investor, Entrepreneur, and Business Builder
Len has built his career around credit investing, business formation, and the development of investment platforms.
In 1998, he founded the business that became Fifth Street. Under his leadership, Fifth Street grew into an alternative credit manager overseeing approximately $5 billion across private investment vehicles and publicly traded companies. In 2017, Oaktree Capital Management assumed management of Fifth Street’s publicly traded business development companies.
Len later founded Tannenbaum Capital Group, a group of affiliated asset managers focused on credit-based strategies, including private credit, opportunistic credit, and real estate lending.
Today, his work brings together the experience of an investor, the perspective of an entrepreneur, and the discipline of a credit underwriter.
Experience Across Credit, Investing, and Entrepreneurship
Private Credit
Len’s private credit experience spans direct lending, middle-market finance, credit underwriting, BDC's (business development companies), and permanent capital, with a track record of investing and deploying capital across multiple credit and economic cycles.
Investing
His investment approach is grounded in rigorous research, disciplined underwriting, and strong alignment of interests, with a focus on evaluating opportunity through both the potential for attractive returns and the careful management of downside risk.
Entrepreneurship
From building Fifth Street into a national investment platform to helping establish Tannenbaum Capital Group, Len’s career reflects an entrepreneurial approach to building businesses, bringing together experienced teams, identifying new opportunities, and transforming investment ideas into scalable enterprises.
Select Career Highlights
Over three decades
Investing in credit and building investment businesses
More than $15 billion
In loans underwritten during his career
Five Public Investment Entities
NYSE and NASDAQ
Over $5 billion
Managed by Fifth Street across private vehicles and publicly traded companies
Len is a graduate of the Wharton School of the University of Pennsylvania, where he completed both his undergraduate and graduate studies through Wharton’s submatriculation program, earning his bachelor’s and master’s degrees on an accelerated academic path. He also holds the Chartered Financial Analyst (CFA) designation.
Featured Perspective
Why Bigger Is Not Always Better in Wealth Management
In an article for Wharton Magazine, Len discusses consolidation in the wealth management industry and explains why scale alone does not guarantee better outcomes for clients.
He explains that successful firms must remain focused on their distinctive strengths, preserve a client-centered culture, and communicate clearly during periods of change.
“Spreading the Wealth”
Wharton Magazine • February 26, 2026
Recent Media
Perspectives on the Changing Private Credit Market
Len recently joined Bloomberg’s Carol Massar, Tim Stenovec, and credit editor James Crombie for a discussion about the rapidly changing private credit market.
The conversation addressed stress within private credit portfolios, payment-in-kind interest, investor liquidity, credit selection, and the opportunities that may emerge as the market changes.
Philanthropy and Community Involvement
Len’s philanthropic interests focus on children’s well-being, education, wildlife conservation, entrepreneurship, and personal development. His support extends to organizations and initiatives that create opportunity, strengthen communities, protect wildlife, and help individuals build the skills and confidence to shape their own futures.