Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) | Capital Allocators – Inside the Institutional Investment Industry

In this episode of Capital Allocators, host Ted Seides interviews Josh Koplewicz, Managing Partner of Thayer Street Partners, a private equity firm focused on providing flexible growth capital to lower middle market companies in financial and business services. Josh discusses his early interest in business and real estate, his experiences at Goldman Sachs, and the evolution of Thayer Street into an institutional platform. The conversation covers Thayer Street's thematic sourcing, deal structuring, portfolio construction, and the challenges of scaling a boutique firm, as well as Josh's vision for the future, emphasizing the growing need for flexible capital in the lower mid-market and the firm's strategy of investing in recurring revenue businesses with downside protection and upside potential.

Outlines

Part 1: Introduction and Early Career

Part 2: Building Thayer Street

Part 3: Investment Strategy and Process

Part 4: Challenges and Support

Part 5: Personal Reflections and Future Outlook

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Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451)

Capital Allocators – Inside the Institutional Investment Industry

Part 1: Introduction and Early Career

Introduction to Josh Koplewicz and Early Interest in Business

Connecting Interests and Early Experiences at Goldman Sachs

Lessons Learned During the GFC

Mistakes Observed During the GFC and the Decision to Launch Thayer Street

Part 2: Building Thayer Street

Early Days of Thayer Street and Building Relationships

Building Relationships and Skill Sets Needed for the Team

Transition to an Institutional Structure and Strategy of Thayer Street

Part 3: Investment Strategy and Process

Opportunities in the Current Market Environment

Themes and the Fragmented Business Landscape

Diligence Process

Structuring Deals and Risk-Reward Framework

Creative Structure Example: Payments and Invoicing Company

Outcome of the Payments Company and Another Creative Structure Example

Part 4: Challenges and Support

What Happens When Investments Don't Go as Expected

Supporting Management Teams and Competing in the Space

Structuring a Portfolio and Potential Risks

Premortem and Business Challenges

Part 5: Personal Reflections and Future Outlook

Closing Questions and Future Goals

Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451)

Capital Allocators – Inside the Institutional Investment Industry

Part 1: Introduction and Early Career

00:00Introduction to Josh Koplewicz and Early Interest in Business

Introduction to Josh Koplewicz and Early Interest in Business

04:51Connecting Interests and Early Experiences at Goldman Sachs

Connecting Interests and Early Experiences at Goldman Sachs

07:00Lessons Learned During the GFC

Lessons Learned During the GFC

09:05Mistakes Observed During the GFC and the Decision to Launch Thayer Street

Mistakes Observed During the GFC and the Decision to Launch Thayer Street

Part 2: Building Thayer Street

13:30Early Days of Thayer Street and Building Relationships

Early Days of Thayer Street and Building Relationships

16:02Building Relationships and Skill Sets Needed for the Team

Building Relationships and Skill Sets Needed for the Team

18:52Transition to an Institutional Structure and Strategy of Thayer Street

Transition to an Institutional Structure and Strategy of Thayer Street

Part 3: Investment Strategy and Process

21:28Opportunities in the Current Market Environment

Opportunities in the Current Market Environment

24:09Themes and the Fragmented Business Landscape

Themes and the Fragmented Business Landscape

27:30Diligence Process

Diligence Process

29:42Structuring Deals and Risk-Reward Framework

Structuring Deals and Risk-Reward Framework

32:16Creative Structure Example: Payments and Invoicing Company

Creative Structure Example: Payments and Invoicing Company

35:53Outcome of the Payments Company and Another Creative Structure Example

Outcome of the Payments Company and Another Creative Structure Example

Part 4: Challenges and Support

39:13What Happens When Investments Don't Go as Expected

What Happens When Investments Don't Go as Expected

41:29Supporting Management Teams and Competing in the Space

Supporting Management Teams and Competing in the Space

43:45Structuring a Portfolio and Potential Risks

Structuring a Portfolio and Potential Risks

47:00Premortem and Business Challenges

Premortem and Business Challenges

Part 5: Personal Reflections and Future Outlook

51:26Closing Questions and Future Goals

Closing Questions and Future Goals