What lesson shapes your investment decisions most?

Josh Kopelman

Founder and Partner · First Round Capital

Identify risks

Josh Kopelman says it's important to identify the risks you're taking, since knowing the areas against you lets you structure a strategy and build a plan around them rather than hiding them.

🚀Michal Rokosz

Partner

Look for anomalies

Michal Rokosz says his job is finding anomalies, because the companies that really break out and become decacorns are anomalies rather than a regular course of action.

Kenan Saleh

Investment Partner · Andreessen Horowitz

Co‑founder dynamics

Kenan Saleh says he looks at whether co-founders have similar life experiences—similar networks, jobs, and schools—even if they haven't known each other long.

GR

Gili Raanan

Cyberstarter · Cyberstarts

One conversation

Gili Raanan says it typically takes him one conversation to decide on an investment, saying that in most cases he knows he's an investor after about 10 minutes.

David Weisburd

Founder · Weisburd Capital

Founders that productize themselves

David Weisburd says one of the best founder archetypes he loves to back is founders who productize themselves, citing Cam Sepa, who turned himself into a product.

The answer starts at 29:40.

MF

Morgan Flager

Managing Partner · Silverton Partners

What could go right without me

Morgan Flager says he asks "what could go right without me," weighing whether a company works without his involvement, paired with asking what if it goes right—which he calls a venture investor's most important attribute to maintain.

IR

Ian Rountree

General Partner · Cantos

Prioritize the team

Ian Rountree says he prioritizes the team, liking to see the team page up front because at Precedent Seed they invest more in people than in the idea, technology, or business.

The answer starts at 22:51.

MG

Miles Grimshaw

Partner · Thrive Capital

Be impatiently patient

Miles Grimshaw says a core ethos of his investment team is to be "impatiently patient": constantly learning, exploring and meeting people, while waiting patiently for the right moments that fit organically.

Guy Katsovich

Co-Founder & Partner · Fusion Vc

Invest in outliers

Guy Katsovich says his practice is to invest in outliers and non-consensus deals, the thesis he pitches to LPs; if they know too much, he says, they may not be serving that thesis.

SK

Steve Kupfer

Partner · Reach Capital

Focus on real problems

Steve Kupfer says he focused on real problems he saw daily, saying he underwrote all his early Red House deals based on those day-to-day problems.

Justin Smith-Lorenzetti

Founder & Managing Director · Intact Private Capital

Relentless ambition

Justin Smith-Lorenzetti says he looks for relentless or unrelenting ambition in the founders he backs, calling it the best way to describe what he’s looking for.

Andrea Hippeau

Partner · Lerer Hippeau

Back the right people

Andrea Hippeau says backing the right people is the practice that resonates with her after a decade in VC, and her mistakes have come from talking herself into founders she lacked a gut feeling about.

Christina Quinn

General Partner · Ssc Venture Partners

Entrepreneur's mindset

Christina Quinn says she bears in mind the entrepreneur's mindset—adaptability, resilience, initiative and self-awareness—when assessing a new founder, because early-stage investing often comes down to belief in the entrepreneur.

Yuval Ariav

Managing Partner · Symbol

Re‑examining assumptions

Yuval Ariav says re-examining assumptions has shaped his approach to deciding investments, since past lessons are rarely immortal as reality, people, technology and markets change; he argues investors should ask whether an assumption still holds.

Mark Peter Davis

Managing Partner · Interplay

Focus on barriers

Mark Peter Davis says he leans a lot on barriers as a concept when assessing companies, even if they don't start with them at day one but layer them in over time.

Jason Gray

Founder & Managing Partner · Pioneer Fund

Unique insight

Jason Gray says he looks for a unique insight in founders—what they see that the rest of the market isn't. He also mentions valuing their rate of progress.