Why venture is unusually difficult today

How do experienced LPs evaluate venture managers in an increasingly crowded and bifurcated market? David Weisburd speaks with Kate Simpson about her career as a venture allocator, her move to GEM to lead venture investing, and how institutional LPs assess sourcing, portfolio construction, and power-law dynamics. Kate explains how reference calls, fund sizing, access, and long-term relationships shape conviction in venture manager selection.

Highlights:

• Kate’s path from the UNC Endowment to leading venture at GEM
• Lessons learned from fund-of-funds investing and institutional due diligence
• Why asking the right questions matters more than having the right answers
• Differentiating between “good” and “glowing” references
• Evaluating venture funds through sourcing, picking, and winning
• The role of portfolio construction and reserve strategy in venture returns
• Why venture has become two distinct games: access vs. discovery
• How fund size impacts the ability to capture power-law outcomes
• Signals LPs use to evaluate managers before liquidity
• The evolving role of LPs as long-term partners in venture ecosystems

Guest Bio:

Kate Simpson is a senior venture allocator at GEM, where she leads venture investing across the firm’s OCIO and discretionary platforms. She has spent her career as an institutional LP, with prior experience at the UNC Endowment and multiple fund-of-funds, focusing on venture manager selection, portfolio construction, and long-term partnerships. Kate brings a deep understanding of both qualitative and quantitative diligence across early-stage and multi-stage venture strategies.

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Sponsor:

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LinkedIn:https://www.linkedin.com/in/kate-simpson-159796/

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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 (0:40) Kate's career and venture investing insights (3:49) Effective reference checks and venture investing strategies (9:50) Fund math and spotting industry shifts (13:25) Evaluating venture funds and market bifurcation (17:24) Sourcing competitive advantages at Gem (20:41) LP vs. GP perspectives in venture capital (22:19) Identifying signs of successful investors (24:14) Challenges with DPI and LP value add (26:29) Building LP pipelines and JEM's approach to relationships (28:35) Active participation and current venture investing difficulties (30:56) Venture returns and the role of solo GPs (34:08) Managing key man risk and long-term GP partnerships (38:17) Career advice and advocating for oneself in investments (39:30) Closing remarks