Concerns about OpenAI's business model

Why does venture capital break when liquidity disappears and what actually creates alpha when markets get hard? In this episode, I talk with Logan Allin, Founder and Managing Partner of Fin Capital, about why private markets are structurally changing, how secondaries are becoming a primary liquidity mechanism, and why discipline — not optimism — is what separates enduring managers from zombies. Logan explains how Fin Capital built a full-lifecycle platform across venture and late-stage secondaries, why fund size is the enemy of performance, and how contrarian positioning creates real structural alpha over time.

Highlights:

• Why venture “breaks” without liquidity
• How secondaries are replacing IPOs as the main exit
• Why fund size destroys returns past a threshold
• The rise of zombie funds and asset gatherers
• How Fin Capital uses secondaries as a risk buffer
• Why competition — not fundamentals — drives private market pricing
• Why retail capital is dangerous for blind-pool venture funds
• How contrarian investing actually works in practice
• Why orchestration and application layers win in AI
• Why alpha comes from doing the work others avoid

Guest Bio:

Logan Allin is the Founder and Managing Partner of Fin Capital, a global venture and growth equity firm focused exclusively on enterprise software for financial services. He previously served as Vice President at SoFi Ventures and has held operating and advisory roles across fintech and financial services, including leadership positions at Atlantic Trust, City National Bank, and several venture-backed startups. Logan holds degrees from Duke University and Stanford Graduate School of Business, where he was a Sloan Fellow.

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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 (1:07) Challenges and dynamics in the current venture market (2:17) Opportunities in the secondaries market and institutional capital (7:02) Diligence process for late-stage pre-IPO opportunities (9:09) Discussion on fund lifespan and size constraints (14:05) Retail investors and OpenAI's business model concerns (19:36) Howard Marks' insights and second-order thinking in investments (22:40) Investment strategies in AI and avoiding LLMs (24:02) LP communication and the cost of being a contrarian (27:08) Conversations with LPs and focus on specific tech sectors (28:32) Emerging spaces in technology investments (32:22) FinCapital's approach to investment and market relations (34:09) Closing remarks