How I Invest with David Weisburd

E399: How General Catalyst Finds Billion-Dollar Startups


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Most investors assume that once a venture firm reaches $43 billion in assets under management, the real opportunities shift toward writing larger checks.
Yuri Sagilov believes the opposite.
General Catalyst continues to push deeper into seed because that's where investment themes are born, founder relationships are formed, and category-defining companies are first recognized. Rather than optimizing for larger deployments, the firm optimizes for ownership, conviction, and seeing the future before everyone else. It's also why General Catalyst intentionally removed signaling risk from its seed strategy, giving founders confidence that early backing won't become a disadvantage later. Throughout our conversation, Yuri explains why AI-native founders think differently, why the best venture firms remain generalists, and why the next decade of venture may look very different from the last.
Highlights:
  • Why General Catalyst believes seed delivers some of venture's best returns.
  • How the firm eliminated signaling risk without sacrificing ownership.
  • Why Anduril changed the way investors think about defense startups.
  • Why today's AI-native founders are building from a completely different starting point.
  • The case for staying a generalist instead of launching sector-specific funds.
  • Why ownership matters more than the size of the initial investment.
  • How private markets could keep the best companies private much longer.
  • The relationship philosophy Yuri says has compounded the most throughout his career.
  • Guest Bio:

    Yuri Sagilov is a Partner at General Catalyst, where he focuses on seed investing across the firm's global platform. Previously, he founded Wayfinder Ventures, a first-check seed fund whose portfolio companies have created more than $23 billion in value.

    Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].

    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.

    Stay Connected with David Weisburd:

    X/Twitter: @dweisburd

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

    Stay Connected with Yuri Sagalov:

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

    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 a $43B Firm Still Bets on Seed
    (2:39) Finding Categories Before They Exist
    (4:00) Learning From Founders Living in the Future
    (5:47) Why Great Seed Investors Stay Generalists
    (8:51) Eliminating Signaling Risk
    (12:08) Building General Catalyst's New Seed Strategy
    (13:27) Inside a 200-Company Seed Portfolio
    (14:40) Does Every Investment Need to Return the Fund?
    (16:05) Recognizing Power Law Companies Early
    (18:04) Why the Best Companies May Stay Private Longer
    (24:50) The Highest Compounding Asset in Venture
    (26:33) Why Yuri Became More Bullish on AI
    ...more
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