Investments & TCG
Building Investment Businesses
Across Multiple Market Cycles
Leonard M. “Len” Tannenbaum has spent his career investing in credit and building the organizations responsible for sourcing, underwriting, and managing those investments.
In 1998, he founded the business that became Fifth Street and developed it into a national alternative credit platform managing over $5 billion across private investment vehicles and publicly traded companies.
Following the Fifth Street transition in 2017, Len focused on family investments and later founded Tannenbaum Capital Group, a group of affiliated asset managers pursuing credit-based strategies.
This page explains Len’s relationship with these organizations and distinguishes his current activities from historical roles.
Building
Investment Businesses
Len’s career has extended well beyond making individual investments. For more than three decades, he has built and led investment businesses—raising capital, recruiting and developing teams, creating lending platforms, leading public companies, and working alongside boards, investors, borrowers, and business owners.
That experience has given Len a perspective that combines the disciplines of an investor with the responsibilities of an entrepreneur and business builder.
According to Wharton Magazine, Len has underwritten more than $15 billion in loans and taken five investment entities public over the course of his career.
- Founded his first private investment business in 1998
- Built Fifth Street into a national alternative credit platform
- Created and managed private funds and publicly traded investment vehicles
- Developed and led BDCs focused on financing middle-market companies
- Navigated multiple credit cycles, periods of market disruption, and changing economic conditions
- Transitioned to investing family capital following Fifth Street
- Founded Tannenbaum Capital Group (TCG) with family members and experienced investment executives
- Built and supported specialized investment businesses across private credit, opportunistic credit, and real estate lending
Across each chapter, Len’s approach has combined investment discipline with entrepreneurship—identifying opportunities, assembling experienced teams, committing capital, and building platforms designed for long-term growth.
The Building of Tannenbaum Capital Group
Len is the Founder of Tannenbaum Capital Group (TCG), an investment platform built around specialized asset managers and credit-oriented strategies.
Following the transition of Fifth Street in 2017, Len focused on managing family capital and investing across credit, equities, and real estate. During the COVID-19 period, he began building a new investment organization alongside his wife, Robyn, members of his family, and experienced investment professionals.
That effort became TCG, bringing together affiliated asset managers focused on private credit, opportunistic credit, and real estate lending.
Len’s role at TCG combines his experience as an investor, entrepreneur, and company builder. He helps shape the organization’s strategic direction, identifies and partners with experienced executives, supports the development of new investment businesses, and commits capital alongside the teams responsible for managing them.
Rather than applying a single investment approach across the organization, TCG is structured around specialized teams and distinct affiliated businesses—allowing experienced investment professionals to focus on their areas of expertise while benefiting from the resources, capital, and strategic support of the broader TCG platform.
A Group of Affiliated Investment Businesses
Tannenbaum Capital Group is not itself presented as a single investment adviser managing every strategy associated with the TCG name.
Instead, TCG refers to a group of affiliated businesses. Certain affiliated entities are registered investment advisers, while others operate under different regulatory or organizational arrangements. Each is a separate legal entity with its own responsibilities.
This distinction matters. Len’s role as TCG’s founder should not be interpreted to mean that every affiliated investment vehicle, adviser, or portfolio company is operated directly by Len or by one undifferentiated TCG entity.
For current information about TCG’s organization, leadership, investment strategies, and regulatory disclosures, visitors should consult the official TCG website and the filings of the relevant investment entity.
Fifth Street
Len founded his first private investment business in 1998 at the age of 27. That business became the foundation for Fifth Street.
Fifth Street initially concentrated on providing debt and structured capital to small and middle-market companies. As the business grew, it expanded its investment capabilities, geographic presence, institutional relationships, and access to private and public capital.
Under Len’s leadership, Fifth Street developed from a small private investment operation into a national alternative credit platform with more than 150 employees and offices in several U.S. markets.
The organization managed approximately $5 billion across private investment vehicles and two publicly traded business development companies.
Len served in senior leadership, investment, and board roles across the Fifth Street organization. His responsibilities included credit oversight, company strategy, capital formation, public-company leadership, and the development of the firm’s investment teams and operating infrastructure.
From Private Funds to Public Investment Vehicles
An important part of Fifth Street’s growth was its expansion from private investment funds into publicly traded companies.
Fifth Street Finance Corp. became a publicly traded business development company focused on lending to small and middle-market businesses. Fifth Street Senior Floating Rate Corp. later provided another publicly traded vehicle focused primarily on senior secured, floating-rate loans.
Fifth Street Asset Management Inc., the asset-management company associated with the platform, also became publicly traded.
Len held various executive and board positions across these organizations. His experience included investment oversight, corporate governance, public reporting, shareholder communications, capital raising, and the management of investment vehicles through changing market conditions.
These were related but legally distinct organizations. The full Fifth Street page will explain the relationships among the asset manager, investment adviser, holding companies, private funds, and publicly traded business development companies.
The Transition
In 2017, Fifth Street entered a major transition.
Oaktree Capital Management assumed the investment-management agreements of Fifth Street Finance Corp. and Fifth Street Senior Floating Rate Corp., the two publicly traded business development companies previously managed by Fifth Street. The companies were subsequently renamed Oaktree Specialty Lending Corporation and Oaktree Strategic Income Corporation.
The transaction concluded Len’s leadership of the Fifth Street platform and marked the end of a business he had spent nearly two decades building.
Following the transition, Len stepped away from institutional asset management for a period and concentrated on managing family capital, evaluating investments, and considering what he wanted to build next.