Why More Housing Supply Isn’t as Simple as It Sounds

Why does affordable housing remain one of the most persistent challenges in real estate? In this episode, Jeannette Friedrich sits down with Bo Diamond, Co-Founder and Managing Partner of Caisson Capital Partners, to unpack the realities of attainable housing, the complexities of municipal politics, and how investors can balance returns with social responsibility. Drawing on his experience serving on a local housing crisis task force, Bo brings unique insights into why the problem is so difficult to solve and where practical solutions may lie.

Key takeaways from this episode:

- The difference between “Affordable Housing” with deed restrictions and “Attainable Housing” or naturally occurring workforce housing.

- Why housing supply constraints are as much a political problem as an economic one.

- The challenges developers face when community stakeholders, activists, and policymakers have conflicting goals.

- Where innovation is most needed across capital stacks, policy frameworks, and development models.

- How value-add strategies are evolving in today’s market, with more focus on quality-of-life improvements than heavy renovations.

- Why sustainable occupancy is often more important than chasing maximum rent growth.

- Lessons from serving on a housing task force, including the realities of navigating public perception, NIMBYism, and municipal politics.

Connect with Bo Diamond

Website: www.caissoncap.com

Email: bdiamond@caissoncap.com

LinkedIn: Bo Diamond

Timestamps

00:00 Introduction and Guest Introduction

01:52 Bo's Journey and Housing Crisis Task Force

04:21 Defining Attainable vs. Affordable Housing

21:33 REITs and Development Challenges

23:27 Evolving Value Add Strategies

32:22 Lightning Round and Final Thoughts

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Credits

Producer: Blue Lake Capital

Strategist: Syed Mahmood

Editor: Emma Walker

Opening music: Pomplamoose

*𝘉𝘭𝘶𝘦 𝘓𝘢𝘬𝘦 𝘊𝘢𝘱𝘪𝘵𝘢𝘭 𝘪𝘯𝘷𝘦𝘴𝘵𝘮𝘦𝘯𝘵 𝘰𝘱𝘱𝘰𝘳𝘵𝘶𝘯𝘪𝘵𝘪𝘦𝘴 𝘢𝘳𝘦 𝘰𝘱𝘦𝘯 𝘵𝘰 𝘢𝘤𝘤𝘳𝘦𝘥𝘪𝘵𝘦𝘥 𝘪𝘯𝘷𝘦𝘴𝘵𝘰𝘳𝘴 𝘰𝘯𝘭𝘺. 𝘛𝘩𝘪𝘴 𝘪𝘴 𝘯𝘰𝘵 𝘢𝘯 𝘰𝘧𝘧𝘦𝘳𝘪𝘯𝘨 𝘵𝘰 𝘴𝘦𝘭𝘭 𝘢 𝘴𝘦𝘤𝘶𝘳𝘪𝘵𝘺 𝘰𝘳 𝘢 𝘴𝘰𝘭𝘪𝘤𝘪𝘵𝘢𝘵𝘪𝘰𝘯 𝘵𝘰 𝘴𝘦𝘭𝘭 𝘢 𝘴𝘦𝘤𝘶𝘳𝘪𝘵𝘺. 𝘗𝘭𝘦𝘢𝘴𝘦 𝘤𝘰𝘯𝘴𝘶𝘭𝘵 𝘸𝘪𝘵𝘩 𝘺𝘰𝘶𝘳 𝘊𝘗𝘈, 𝘢𝘵𝘵𝘰𝘳𝘯𝘦𝘺, 𝘢𝘯𝘥/𝘰𝘳 𝘱𝘳𝘰𝘧𝘦𝘴𝘴𝘪𝘰𝘯𝘢𝘭 𝘧𝘪𝘯𝘢𝘯𝘤𝘪𝘢𝘭 𝘢𝘥𝘷𝘪𝘴𝘰𝘳 𝘳𝘦𝘨𝘢𝘳𝘥𝘪𝘯𝘨 𝘵𝘩𝘦 𝘴𝘶𝘪𝘵𝘢𝘣𝘪𝘭𝘪𝘵𝘺 𝘰𝘧 𝘢𝘯 𝘪𝘯𝘷𝘦𝘴𝘵𝘮𝘦𝘯𝘵 𝘣𝘺 𝘺𝘰𝘶.

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