Sizing Investments Over Being Right

Is AI the biggest risk to equity portfolios or the biggest opportunity? In this episode, I talk with Christopher Vogt about how institutional investors think about risk, portfolio construction, and manager selection across public and private markets. We discuss AI disruption, why governance and structure matter more than asset labels, and how to evaluate managers using both quantitative and qualitative frameworks. Chris also shares lessons from building an endowment style portfolio from scratch, why patience matters in private markets, and how position sizing can make or break long term outcomes.

Highlights:

• Why AI is both a major risk and opportunity across equities
• Concerns around SaaS disruption and software private equity
• Structurally higher inflation and long term interest rate outlook
• Organizing portfolios by risk instead of asset class
• Building an endowment style portfolio with conservative risk
• Quant vs qualitative manager selection
• Why models are useful but always flawed
• Reference calls as the most important diligence tool
• Culture and turnover as leading indicators of manager quality
• Vintage diversification and capital pacing in private markets
• The reality of longer venture fund durations
• Quant strategies vs fundamental investing in public markets
• Why position sizing matters more than being right

Guest Bio:

Christopher Vogt is an institutional investor at the Margaret A. Cargill Philanthropies where he oversees public and private equity investments. He has extensive experience across asset allocation, manager selection, and portfolio construction, with a focus on building long term, endowment style portfolios. His approach combines quantitative rigor with deep qualitative judgment, emphasizing governance, culture, and risk management as key drivers of investment success.

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

Sponsor:

AlphaSense is the market intelligence platform trusted by 85% of the S&P 100 that helps you make confident, data-driven decisions faster than your competitors. With powerful search capabilities designed for hedge funds, mutual funds, and private equity investors, AlphaSense gives you the edge to elevate your research. Visit: alpha-sense.com/howiinvest.

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Stay Connected with Christopher Vogt:

LinkedIn:https://www.linkedin.com/in/christopher-vogt-70a62b/

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) Everything Is at Risk (But No One Wants to Admit It) (2:11) The One Macro Shift That Changes Markets for Decades (4:00) Why AI Is a Threat to Every Industry (Not Just Tech) (5:24) The Surprising Jobs AI Can’t Replace (6:09) Why Most Portfolios Are Built Completely Wrong (9:42) Why the Best Investors Don’t Trust Models (14:32) The Most Important Signal in Investing That Everyone Ignores (17:31) What You Learn in 30 Seconds That Data Never Shows (23:03) Why You Shouldn’t Invest Even When It Feels Obvious (31:04) Venture Capital Is Quietly Splitting Into Two Worlds