July 20, 2026

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

1 hour 15 minutes

The best venture investors don't just identify great markets. They recognize exceptional founders before everyone else does.

Michael Gilroy shares lessons from investing at Coatue, Microsoft's M12, Battery Ventures, Insight Partners, and now Marathon Management Partners. He explains what separates extraordinary founders from everyone else, how venture investors evaluate conviction versus consensus, why AI is changing the investment landscape, and how decades of experience shaped his founder-first investing philosophy.

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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We’d like to thank AlphaSense for sponsoring this episode!

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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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.

(0:00) Why the Best Venture Firms Think in Decades

(2:17) The Biggest Mistake Founders Make When Building Boards

(5:46) Why Great Board Meetings Aren't About the Past

(9:12) The Simple Change That Makes Every Board More Valuable

(13:41) How Incentives Quietly Shape Venture Capital

(18:25) Why the Best Investors Measure People, Not Just Companies

(23:08) The Hidden Cost of Growing Too Fast in Venture

(28:16) The Framework Behind High-Performing Startup Boards

(30:37) The Truth About Second-Generation Investors

(36:45) The Leadership Trait That Separates Elite Investors

...more

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By David Weisburd

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