Patient Capital, Bold Bets: Constructing a Venture Book That Works

This week on Swimming with Allocators, Joshua Berkowitz of Berkocorp joins Earnest and Alexa to share his journey transitioning his family office from real estate to venture capital, offering candid insights on building relationships with top VC and PE managers, the importance of patience and long-term thinking, and the realities of portfolio construction. The discussion covers how to underwrite exceptional managers, the value of GP and LP recommendations, and the evolving landscape of venture, especially the rise of young founders and AI-driven startups. Listeners will also hear from Shane Goudey from Sidley on trends in fund formation and the current state of the venture market. Key takeaways include the need for genuine interest and commitment in venture investing, the benefits of a diversified yet opportunistic portfolio, practical advice for family offices considering this asset class, and so much more. 

Highlights from this week’s conversation include:

• Joshua’s Background and Transition From Real Estate to Venture Capital (0:12)
• Diversifying from Real Estate to Venture (1:43)
• Commitment and Learning Curve in Venture Capital (3:45)
• GP References vs. LP Recommendations (5:36)
• Reflections on First Investments & Portfolio Design (7:24)
• Deployment Strategy and Allocation Modeling (10:53)
• Fund Formation Market Trends and Sponsor’s Perspective (16:21)
• Underwriting Individual GPs & What Makes a Good Manager (18:11)
• Suitability and Motivation for Family Offices in Venture (20:57)
• Return Expectations and Investment Strategy (24:55)
• Challenges with Fund Lives & Reclassifying Mature Assets (27:21)
• Trends: Resurgence of Young Founders & AI (29:45)
• Closing Thoughts and Next Steps for Berkocorp (33:11)

Berkocorp is a Canadian family investment office managing a Vancouver-based real estate portfolio and actively backing top venture capital and private equity managers across North America. Led by Managing Principal Joshua Berkowitz, Berkocorp takes an independent, long-term approach to capital partnerships, with a portfolio spanning micro VCs to billion-dollar growth funds. Learn more at www.linkedin.com/company/berkocorp.

Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com.

Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. 

The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only.

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