AI-enabled tax-aware investing

Why are vertical AI applications emerging as some of the most defensible opportunities in technology today? David Weisburd speaks with Nick Beim about why context—not raw intelligence—is becoming the key driver of AI performance, and how vertical software is reshaping wealth management, legal services, and defense. Nick shares how legacy infrastructure, industry economics, and human-centered workflows create enduring opportunities for AI-driven transformation.

Highlights:

• Why vertical AI outperforms horizontal models through domain-specific context
• The limits of large LLM platforms in winning every application layer
• Structural failures in wealth management technology and custody systems
• Why advisors remain central despite advances in automation
• AI-driven tax-aware investing and personalization at scale
• The next wave of legal tech beyond basic research tools
• Why high legal costs suppress economic activity—and how AI changes that
• How AI is reshaping defense, intelligence, and modern warfare
• Low-cost autonomous systems vs. traditional defense contractors
• Why pattern recognition fails for the most disruptive venture investments

Guest Bio:

Nick Beim is a Partner at Venrock, where he has invested for over two decades across AI, wealth management, fintech, legal tech, and defense technology. He previously worked at McKinsey & Company and Goldman Sachs and serves on the Council on Foreign Relations. Nick is known for backing category-defining companies, focusing on vertical software, and investing in founders building highly contextual, defensible businesses.

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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 Nick Beim:

LinkedIn: https://www.linkedin.com/in/nickbeim/

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 (1:13) Limitations of horizontal LLMs and wealth management tech (5:34) Context in financial advising and rise of retail alternative investments (10:02) AI's future in tax-aware investing and legal tech (15:04) AI's impact on defense, national security, and next-gen warfare (21:36) Competition in defense tech and methodologies for diligencing AI investments (25:01) Pioneering companies and strategies for niche market investments (27:16) Advice for early career venture capitalists and understanding power law (31:32) Characteristics of successful founders and the role of personal drive (36:30) Founder magnetism, charisma, and the importance of transparency (38:31) Closing remarks