What principle guides your risk approach in investment decisions?

David Weisburd

Founder · Weisburd Capital

Stay in the game

David Weisburd says rule one is to stay in the game and rule two is don't break it, because giving up some of your turn to stay in is good for you, investors, and your brand, which compounds.

The answer starts at 41:50.

🚀Michal Rokosz

Partner

Seek anomalies

🚀Michal Rokosz says his job is to find the anomalies, since the companies that become decacorns are outliers rather than the regular course of action, so he is skeptical of founders who do everything by the book.

RM

Rajeev Mantri

Founder / Managing Director · Navam Capital

Never overpay

Rajeev Mantri says one should never overpay, because overpaying for an asset makes that investment dead on arrival and you can never claw it back or make it good again.

The answer starts at 34:01.

Bill Ackman

Founder and Chief Executive Officer · Pershing Square Capital Management

Assess risk

Bill Ackman says the most important thing an investor has to do is assess the risk, reasoning that a business's value is the present value of the cash it generates over its life.

KV

Krishna Visvanathan

Co-founder & Partner · Crane Venture Partners

Bet big early

Krishna Visvanathan says his firm's philosophy is to go early and bet on things that could be very large, taking as much risk as possible because they want an even bigger outcome.

MF

Morgan Flager

Managing Partner · Silverton Partners

What could go right

Morgan Flager says the most important attribute for a venture investor is asking “what if it goes right,” because people can get caught up in what could go wrong and forget the upside.

Brian Singerman

Partner · Founders Fund

No checklist, follow intuition

Brian Singerman says he has no checklist or rubric at all, since attempts to define founders-fund attributes never worked or proved accurate; he just looks for people who spike with him, differently each time.

Guy Katsovich

Co-Founder & Partner · Fusion Vc

Embrace uncertainty

Guy Katsovich says he embraces uncertainty: he invests where he doesn't know if it will be big or go home, because being really confident means they aren't doing their job right.

SK

Steve Kupfer

Partner · Reach Capital

Be comfortable taking risk

Steve Kupfer says his approach is to be comfortable taking risk: as an early-stage venture capitalist, if you're not comfortable taking risk you're in the wrong business, and it's what they're compensated and funded on.

Justin Smith-Lorenzetti

Founder & Managing Director · Intact Private Capital

Back relentless, unstoppable founders

Justin Smith-Lorenzetti says he backs founders who seem like killers who won't let their idea die, because choosing right can generate an outsized return for the fund.

Andrea Hippeau

Partner · Lerer Hippeau

Don’t be afraid to look stupid

Andrea Hippeau says her guiding risk principle is not being afraid to look stupid, since contrarian investments seem stupid on their face and that is how they find alpha.

Yuval Ariav

Managing Partner · Symbol

Question assumptions

Yuval Ariav says his guiding principle is to question assumptions, because reality changes and few past lessons are immortal, so he asks whether an assumption still holds.

David Frankel

Managing Partner · Founder Collective

Patience and discipline

David Frankel says patience and discipline guide his investment decisions, because he pushes back on the go-go-go mentality and some great companies just take time to mature.

Sam Altman

Chief Executive Officer · OpenAI

Seek contrarian conviction

Sam Altman says to seek contrarian conviction: develop reasonable conviction in things conventional wisdom says are wrong and accept it may take a long time, because conventional wisdom is often wrong about what matters most and dismissal buys time.

AR

Dr. Andre Retterath

General Partner · Earlybird Venture Capital

Avoid false negatives

Dr. Andre Retterath says he avoids false negatives, because the cost is asymmetric: saying no to a company that could return 50 times is far more expensive than a false positive where he loses money once.

Focus on upside

Matt Murphy agrees with focusing on upside rather than downside mitigation, saying that doubt from yourself or others makes you dramatically worse, so they try to build a high-trust environment.