E405: Why AI Has Made Venture Capital Harder (Not Easier)

Highlights:

• Why the best venture investments begin with founders instead of markets.
• The founder characteristics Michael consistently looks for before investing.
• Lessons from investing across Coatue, M12, Battery Ventures, and Insight Partners.
• Why consensus thinking often produces average venture returns.
• How AI is reshaping the next generation of technology companies.
• The difference between backing great businesses versus great founders.
• Why founder obsession matters more than polished presentations.
• How exceptional venture investors develop long-term conviction.
• The lessons Michael carried into launching Marathon Management Partners.
• Why founder-first investing continues to outperform market-first investing.

Guest Bio:

Michael Gilroy is the Founding Partner of Marathon Management Partners, where he invests in exceptional technology companies across venture and growth stages. Before launching Marathon, he was a General Partner at Coatue, investing across both private and public technology markets. Earlier in his career, he held investing roles at M12 (Microsoft's Venture Fund), Battery Ventures, and Insight Partners, developing deep expertise in enterprise software, AI, and technology investing. Today, Michael brings a founder-first perspective shaped by decades of experience backing category-defining companies alongside many of the industry's leading investors.

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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.

Stay Connected with David Weisburd:

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

Stay Connected with Micheal Gilroy:

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

Questions or topics you want us to discuss on How I Invest? Email us at [email protected].

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 Pierce. 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.