How does an early-career venture investor best develop judgment about what a great company looks like?

Christa Quarles · Jul 29, 2021

Working in equity research/banking meeting hundreds of growth companies builds pattern recognition for identifying winners better than working inside a single company

High sample size — she met CEOs daily and had to judge which companies would IPO, learning business models and leadership profiles across hundreds of companies rather than seeing just one

Scope: based on her own experience around 2000

2:49 20VC: A Masterclass in Leadership and Scaling Companies: The Decisions only the CEO Can Make, The Secret To Talent Acquisition and Retention and How To Find The Unscalable Things that are Fundamental To Scale with Christa Quarles, CEO @ Corel Corporation

Trae Stephens · Apr 3, 2024

New investors should take as many pitch meetings as possible with no filtering standards, because judgment can only be developed through volume

Brian Singerman's advice: you only start perceiving what's good and bad, and can only run a reliable founder check, after high volume; being selective early is impossible because you lack the pattern

Scope: applies to an investor's first year

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Harry Stebbings · Jun 17, 2024

New investors should do few deals but meet many people

You need volume of meetings to develop a benchmark for what great entrepreneurs look like; without meeting many you never build that muscle, even though you'll still often be wrong

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Delian Asparouhov · Jul 29, 2024

In your first year in venture you should open your aperture and meet almost any founder, but stay judicious about actually doing deals until you've developed taste for greatness — roughly after a thousand founder meetings

You need a dataset large enough, ideally containing founders of the caliber of Parker Conrad, Eric Kleinman and Alex Wang, before you can recognize what greatness looks like

Scope: applies to a first-year junior investor

26:16 20VC: Twitter's Most Controversial VC Delian Asparouhov on Inside the Walls of Founders Fund: What the World Does Not See | Why Western Europe Will Be Like the Third World | Why SaaS as an Industry Might Be Dead

Harry Stebbings · Nov 21, 2025

The most important thing for anyone entering venture is to meet as many founders as possible, in order to establish a benchmark of what good looks like

Establishing the benchmark of what good is is one of the most important things you can do early in a venture career

Scope: advice for people early in a venture career

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Michael Eisenberg · Dec 6, 2021

The biggest source of learning in venture is the people around you — partners and entrepreneurs — rather than analyzing your own successes or failures

He has learned most from sitting around the table with smarter partners and from talking to entrepreneurs daily; the job allows continuous learning from people

Scope: personal experience

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Max Altman · Nov 21, 2025

Early, close exposure to top-tier founders and investors is the best training an investor can get because it teaches you where the bar actually is

Living and working around people like Peter Thiel, Keith Rabois, and the founders of Instacart, Reddit, Rippling and Boom showed him what a top-decile company looks like, so he learned the benchmark

12:05 20VC: Max Altman on The New Seed War: Can Anyone Compete with Sequoia and a16z | Leaving $2BN on the Table with Reddit | Lessons from Backing Rippling at $25M Post | Why Climate Tech is a Mirage and Disaster

Pat Grady · Jul 8, 2024

The way to get better at picking is apprenticeship: experienced investors doing the work in the field alongside junior investors, ideally exposing them to many different partners rather than one

Venture is an apprenticeship business; working alongside Doug Leone, Jim Goetz, Roelof Botha and Michael Moritz across many repetitions let him see how each of them thought and work out how he wanted to think about an investment

26:09 20VC: The Sequoia Investment Process | Investing Lessons from Doug Leone, Roelof Botha & Alfred Lin | Sequoia's Framework for Analysing Founders | The True Benefit of Having Sequoia on a Cap Table & Sequoia's Biggest Threat with Pat Grady

David Cahn · Aug 5, 2024 · hedged

The best way to develop as an investor is to identify each great colleague's specific superpower and the behaviors behind it, and aim to become ~80% as good at it — being 80% as good as ten people at ten superpowers makes you very good

You are unlikely to fully match someone at their own superpower, but stacking many partial masteries compounds into broad strength

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Mark Suster · May 1, 2024

New venture investors should deliberately slow down and see hundreds of deals before deploying, because the first deals that look good are almost certainly not the ones you should do

Writing checks is easy; driving returns is hard. Looking at 7 deals yields 3 that look good, 70 yields 3-4, 700 yields 7-10 — but the chance the first three are the right ones is almost zero, so pattern recognition requires volume

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Tom Hulme · May 8, 2024

Learning to be a venture investor is measured in deals and time, not dollars — roughly five deals over five years is the minimum to start seeing patterns

The learning cycle is number of deals plus time to see how they perform; a dollar figure is meaningless because what $20M buys changes drastically across eras (it was a pre-seed in 2020)

Scope: five deals is a minimum, not sufficient; he says he still doesn't know if he's any good after ~25 deals

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Mitchell Green · Mar 28, 2025

You only learn what a good company looks like by cold-calling and talking to thousands of bad ones, an experience that gets distilled into a handful (~five) of screening criteria such as revenue scale, growth rate and gross margin.

In an effectively unlimited universe of companies you can call, a rigid framework is what keeps judgement calibrated rather than arbitrary.

4:58 Cold calling thousands of bad companies distills into a few screening criteria

Rick Zullo · Aug 23, 2023

Investors should down-select ruthlessly to meetings that could change their life — fund-returning outcome potential, a company inside their top thesis ideas, or a once-in-a-generation founder — and accept missing many great companies

Being meticulously thesis-driven lets him focus on winning the companies that are the best fit for his approach rather than chasing everything

37:40 Down select ruthlessly to meetings with life changing potential accepting many misses

Immad Akhund · May 12, 2025

The way to learn an unfamiliar sector is to make a couple of investments in it, because the process forces conversations with roughly ten people at the edge of that field

Making one or two investments requires speaking to about ten practitioners, and those people teach you the market quickly

38:58 Making investments in a sector forces the learning conversations needed

Kevin Hartz · Jul 22, 2024

Encyclopedic knowledge of the lineage of companies and investors is incredibly important, not useless trivia

37:39 Encyclopedic knowledge of company and investor history builds judgment

Danny Rimer · Jun 17, 2024

New venture partners should resist the urge to put points on the board and instead take their time, make very few bets, and think through every meeting

The visceral instinct is to invest a lot and kiss every frog, but a new partner has no personal bar yet — the bar is the firm's bar, so they should hold to it rather than build volume

41:32 New partners should make very few bets and defer to the firms existing bar

Danny Rimer · Jun 17, 2024

You should meet many people but distribute your time very unequally — heavy time with the clearly exceptional, limited time with those still figuring out what to do

42:22 Distribute meeting time unevenly toward the clearly exceptional