Where Were You When I Was Broke?
What if I'm the Best (but don't know it)?
The Right Time to Start is "Right Now"
Creating A Go To Market Strategy
A Simple Trick for Less Awkward, More Effective One-on-One Meetings
Types of Crowdfunding: Donation, Rewards, and Equity-Based
How To Create A Business Model Canvas
How Startup Funding Stages Work
Everything You Need to Know About Product-Market Fit
Sole Proprietorships: What You Need to Know
Revenue Model
Private Investors for Startups: Everything You Need to Know
Why Founders Can't Retire
The Most Expensive Equity Doesn't go to Investors
How to be Great at Worrying
Top 10 SaaS PPC Agencies (2026)
Equity Is the Most Expensive Currency Your Startup Has. Stop Treating It Like Bar Peanuts.
Can Startups Be a Team of One?
Why are We Really Building a Startup?
We Rarely "Control" Our Startups
The Problem With Never Being Done
What Should My Expectations Be?
What Actually Happens if I Run Out of Gas?
The Value of Side Quests
The Key to Success Is Mastering Failure
We Can't Predict the Future Anymore
We Wanted Efficiency. We Got Isolation.
Startups are the Future of Employment
The Founder "Hard Reset"
Where Does Our Optimism Come From?
When Popularity Destroys Productivity
Will Getting Bigger Make Us Better?
"Just Be Yourself" is Terrible Startup Advice
Embrace How Messed Up You Are
The Great Remote Workplace Reset
Can I Hire Someone to Run My Startup for Me?
How Founders Get "Fired by Promotion"
Burnout is a Treatable Injury
Stop Pretending You Don't Have Enough Time
Are We Aligned with Everyone Around Us?
Will the Payout be Worth the Sacrifice?
How Founders Blow Their Fortunes
When Should We STOP Asking for "More"?
Can Entrepreneurship Help Alleviate Poverty?
Should Employees Really be Our Friends?
Can Founders be Replaced by AI?
The Best Startup Fractional CMOs and Growth Leaders
The Best Growth Marketing Agencies: How to Choose Them and Who They Are
What if We Run Out of Goals?
Reinvention is Our Only Constant
We're So Connected — And Totally Lonely
The 10 Best Growth Agencies for Startups
My Roadmap to Becoming a Confident Leader
Is College a Waste of Time for Founders?
Are We Preventing Our Startup From Evolving?
Building a Startup That Loves You Back
When Our Friends Resent Our Success
When Our Startup Outgrows Us
When Being in the 1% Feels like Failure
We Need Outside Interests that Consume Us
If You're Not Terrified, You're Doing it Wrong
Why do Founders Suck at Asking for Help?
The Ideal Client Profile Is Your Startup’s North Star (Stop Ignoring It)
Are We Growing or Just Getting Fat?
Let's Get Back to Our Why
Does Startup Success Validate Us Personally?
How We Secretly Lose Control of Our Startups
Should Kids Follow in Our Founder Footsteps?
The Evolution of Entry Level Workers
Assume Everyone Will Leave in Year One
Stop Listening to Investors
Was Mortgaging My Life Worth it?
What's My Startup Worth in an Acquisition?
When Our Ambition is Our Enemy
Are Startups in a "Silent Recession"?
The 5 Types of Startup Funding
What Is Startup Funding?
Do Founders Deserve Their Profit?
Michelle Glauser on Diversity and Inclusion
The Utter STUPIDITY of "Risking it All"
Committees Are Where Progress Goes to Die
More Money (Really Means) More Problems
Why Most Founders Don't Get Rich
Investors will be Obsolete
Why is a Founder so Hard to Replace?
We Can't Grow by Saying "No"
Do People Really Want Me to Succeed?
Is the Problem the Player or the Coach?
Will Investors Bail Me Out?
The Value of Actually Getting Paid
Wait a Minute before Giving Away Equity
You Only Think You Work Hard
SMALL is the New Big — Embracing Efficiency in the Age of AI
This is BOOTSTRAPPED — 3 Strategies to Build Your Startup Without Funding
Never Share Your Net Worth
A Steady Hand in the Middle of the Storm
Risk it All vs Steady Paycheck
How About a Startup that Just Makes Money?
How to Recruit a Rockstar Advisor
Why Having Zero Experience is a Huge Asset

Venture Capitalists, Cognitive Bias, And The Dangers Of Learning From The Past

SM
Sonya Mann
Venture Capitalists, Cognitive Bias, And The Dangers Of Learning From The Past

Today we’re exploring how cognitive bias affects venture capitalism. The topic is worth our time because investing is just as much art as it is science.

A venture firm works from a thesis, but a thesis is just a set of proposed understandings. Beneath the graphs and pie charts, the empirical anchors, lie fuzzier things like intuition, hope, and bias.

Let’s understand that bias to better understand why money gets allocated the way it does.

3424215625_fa57eb10ba_b-1

Brains Full of Bias

The human mind is prone to quirks of thought that distort reality. A fun example is the IKEA effect: the tendency to over-value items that you assembled yourself. The planning fallacy is another cognitive bias, one that software developers are familiar with, at least in practice — people are generally too optimistic about the time it will take to complete a project.

Cognitive biases can be combatted when you’re aware of them, but it’s hard to wrap your mind around something that your mind evolved to not wrap around. One ironic example is the bias blindspot: we tend to consider ourselves less biased than others. That makes cognitive biases all the more dangerous, unless you can convince yourself that you really don’t know what you don’t know.

A cognitive bias that’s particularly relevant to venture capitalists is survivorship bias: the tendency to only look at winners, not losers, and then extrapolate the criteria for success from the shared characteristics of the winners.

“When failure becomes invisible, the difference between failure and success may also become invisible,” writes David McRaney, who has cataloged various types of self-delusion since 2009.

For example, if you were just focused on the founders of Facebook and Google, you might assume that entrepreneurs who were undergrads on the eastern side of the United States are more likely to build incredibly valuable companies, ignoring the many failed startups founded by Ivy League alums.

That’s a spurious example, but name-brand degrees may actually have some bearing on how VCs assess founders.

How Vulnerable The VC?

Venture capitalists are particularly susceptible to cognitive biases, says Patrick Mathieson, a partner at Toba Capital.

“[The field] has a couple of things that conspire to make it really awful for survivorship bias, confirmation bias, all these sorts of things that screw up how people think about things,” Mathieson explained on the phone to Mattermark. “The number of observations, the number of trials you’re making, is very small.”

For instance, over ten years, a VC might only invest in fifteen different companies. To make matters worse, the feedback cycles are long.

“You may not know for five years if an investing decision you made is good or not,” Mathieson pointed out.

In other words, working in venture capital means assessing your performance in the exact opposite of ideal conditions for learning. Startups themselves prize quick iteration and continuous development, but VCs aren’t able to use, say, agile methodology.

“There are probably people who have been doing this for twenty years, [but it’s] still unclear if they’re any good at it,” Mathieson said, adding that he includes his own firm.

What About Pattern Matching?

We frequently discuss pattern-matching in this industry, especially when it comes to diversity. But VCs pattern-match to all kinds of characteristics. That’s part of how startup fads develop. But investors also pay attention to many other factors: whether an entrepreneur has industry experience, which group of angels anchored the seed round, or what the metrics should look like when a consumer startup is gaining traction.

Less than a year after Andreessen Horowitz was founded, Ben Horowitz wrote about VCs’ bad habits, and he discussed the pros and cons of pattern-matching:

As a VC, I have come to understand the value of ‘VC pattern matching.’ Experienced VCs have been on dozens of boards and seen thousands of deals. As a result, they recognize patterns of strategy and behavior that generally work, and patterns that generally fail. This is very valuable information for an entrepreneur who, if lucky, only sees one deal in his career.”
However, Horowitz continued, “A pattern-matched instruction without a rationale provides very little help. Either admit that you are pattern matching and that pattern matching is limited, or explain yourself.

Michelle Tandler, an associate at Trinity Ventures, emphasized that her firm uses “pattern-matching based on many factors.” Many of them have to do with the startup’s actual performance, especially beyond the seed stage.

“At the Series A level we’re looking at things like, ‘Can this person get funded for Series B?’,” said Tandler. “We dig really deep into the business model, into the unit economics, into the metrics, into the market they’re going after.”

Founders’ personal character is also key. They need to be driven, organized, and familiar with the market they’re entering.

“We’re doing like fifteen background calls on people,” she remarked, “You’re probably just as likely to get investor attention if you were a product manager at a top tech company as if you had a degree from a top school.”

The Investor’s Pain

VCs do have an incentive to identify their cognitive biases and any other blind spots. “That is one of the things that keeps us up at night,” Tandler said. “That’s the pain of being an investor.” And if you can clear up your firm’s blind spots faster than your competitors can clear theirs, you have an advantage.

“It’s all about not going after the stuff that everyone else is going after.”


This article was originally shared on Mattermark.

Find this article helpful?

This is just a small sample! Register to unlock our in-depth courses, hundreds of video courses, and a library of playbooks and articles to grow your startup fast. Let us Let us show you!

OR
GoogleLinkedInFacebookX/Twitter

Submission confirms agreement to our Terms of Service and Privacy Policy.