Mitigating tail risks through behavior checks

Why does today’s venture market feel increasingly untethered from historical precedent? David Weisburd speaks with Narayan Chowdhury about structural shifts in venture capital, the limits of data-driven decision-making, and how founders and investors navigate an unusually noisy and fragmented market. Narayan shares how access, trust, and long-term relationships are becoming more important as traditional signals lose reliability.

Highlights:

• Why the current venture market feels unprecedented and difficult to underwrite
• Structural gaps in venture data and challenges in finding ground truth
• The role of access and founder selection in venture outcomes
• How regime shifts reduce the usefulness of backward-looking analysis
• Why founder trust and long-term relationships matter more than branding
• The risks of overfished strategies and consensus thinking
• Differences between generalist and specialist venture approaches
• How institutional LPs evaluate manager behavior through market cycles
• Why small teams can now build and scale faster than ever

Guest Bio:

Narayan Chowdhury is a Co-Founder and Partner at Franklin Park, a Philadelphia-based investment firm overseeing approximately $21 billion in assets. He has over two decades of experience allocating capital across venture and private markets, with a focus on manager selection, long-term partnerships, and disciplined portfolio construction amid evolving market regimes.

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Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

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

Stay Connected with Narayan Chowdhury:

LinkedIn: https://www.linkedin.com/in/narayan-chowdhury/

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 (0:14) The unpredictable nature of the current investing landscape and the bipolar market (5:19) The reliability of data and the importance of channel checks in venture capital (9:00) Untethered investments, founder's equity, and long-term investor relationships (13:33) Maintaining investment discipline and the role of media in venture capital (16:29) Balancing high expected returns with operational stability (19:23) The importance of references and continuous market engagement (24:00) Continuous market engagement with Bright Mind in cybersecurity (27:30) Impact of high-velocity capital deployment on firm strategies and venture dynamics (33:15) The importance of long-term relationships and high conviction beliefs in venture capital (36:54) Conclusion and final thoughts from Narayan Chowdhury (37:05) Closing remarks