How do investors balance risk and opportunity in uncertainty?

David Weisburd

Founder · Weisburd Capital

Disciplined Trimming

David Weisburd argues investors should manage risk by systematically trimming positions as valuations rise—using metrics like revenue multiples and selling portions via secondaries or tender offers—while accepting risk can’t be eliminated.

The answer starts at 39:24.

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Bilal Zuberi

Founder and Managing Partner · Red Glass Ventures

Diversify Risk Profiles

Bilal Zuberi says he builds a basket of different risk profiles, taking different types of risk, so that if existential risk spikes across the portfolio, the risks balance out and he still makes money.

The answer starts at 1:08:31.

Shiv Verma

Chief Financial Officer · Robinhood

Risk‑Adjusted Framework

Shiv Verma says investors should use a risk-adjusted framework, taking big bets while understanding the downside, because portfolio managers were evaluated on risk-adjusted returns like Sharpe and information ratios.

Jeff Morris Jr.

Founder & General Partner · Chapter One

Many Small Checks

Jeff Morris Jr. says to diversify with many smaller checks so that the ones that work and the ones that don't don't sink you.

The answer starts at 1:19:27.

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Matt Murphy

Partner · Menlo Ventures

Focus on Upside

Matt Murphy agrees with focusing on upside optimization over downside mitigation, saying it applies at both firm and individual levels and that doubt can make you dramatically worse.