How 2008 Shaped Philip's Investing

How do you turn distressed opportunities into structural alpha—again and again—in an asset class most investors still misunderstand? In this episode, I’m joined by Philip Benjamin, Co-Founder and Managing Partner of Colzen Capital, about how he built a differentiated pre-exit liquidity strategy that serves founders, executives, and investors simultaneously. Philip shares how his fourth-generation real estate background and the 2008 financial crisis shaped his investing worldview, how he applies a distressed-real-estate mindset to late-stage ventures, and why Colzen’s structured equity financing model creates downside protection, aligned incentives, and access to elite companies long before IPO. We also discuss portfolio construction, expected return math, founder psychology, and why this emerging asset class is quietly becoming massive.

Highlights:

• How the global financial crisis shaped Philip’s investment philosophy
• The real-estate insight that led to Colzen’s equity financing model
• How Philip helped create a solution for executives facing the 90-day exercise deadline
• Why founders want liquidity without selling—and how Colzen solves that
• The investor’s advantage: downside protection, PIK interest, and equity participation
• Why late-stage venture outcomes cluster between 0.7x–3x—and how to systematize that
• Understanding structural alpha vs. manager alpha in Colzen’s model
• How to underwrite companies past binary risk and still outperform
• The psychology of founders choosing Colzen over selling secondary
• Why pre-exit liquidity is already a $60B asset class
• Education as the bottleneck—and why this market will become mainstream
• Why diversification across industries matters even within structured finance
• Building long-term LP relationships and evolving from Fund I to Fund II
• Creating win-win transactions: non-zero-sum liquidity for founders and investors
• The family-office analogy of planting, harvesting, and replanting new seeds

Guest Bio:

Philip Benjamin is the Co-Founder and Managing Partner of Colzen Capital, where he leads one of the most innovative structured equity financing strategies in the late-stage venture ecosystem. Philip’s investment philosophy is informed by his fourth-generation real estate family background and by experiencing the 2008 financial crisis just as he graduated college. His family’s timely liquidity event before the crash enabled him to explore private alternatives and eventually develop a distinctive approach to venture risk.

Before launching Colzen, Philip invested across fund managers, direct deals, and special situations, eventually partnering with Sam Buleau to refine a pre-exit liquidity model that supports founders and executives without forcing them to sell shares. Philip applies a distressed-real-estate mindset to venture—focused on downside protection, valuation discipline, and structured upside—and has become a leading voice in the growing pre-exit liquidity asset class.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

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Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Philip Benjamin:

LinkedIn: https://www.linkedin.com/in/philip-h-benjamin/ Colzen Capital: https://www.linkedin.com/company/colzen/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction (1:12) Transitioning to private alternatives and founding Colson (2:16) Mentorship and early real estate investment strategies (4:17) Creation of the equity financing model and navigating market crashes (6:34) Fund formation, strategy, and comparison to private equity (8:03) Value proposition for founders and executives (11:22) Investment strategy, decision-making, and expected returns (18:01) Evolution from Fund One to Fund Two and structural alpha (21:48) Expanding investor access and synergy in the venture space (24:10) Trends in pre-exit liquidity solutions and staying private (27:36) LP feedback and the importance of diversification (33:55) Relationship management and collaboration opportunities (37:50) The family office business and value creation (40:49) Decision-making and planning for future generations (41:32) Closing remarks