Exceptional-Difficult Founder Matrix
Classify founders by exceptional ability and ease of collaboration
- Difficulty
- Easy
- Time to result
- ~weeks to results
- Steps
- 4
- Confidence
- 96%
Don Valentine's two-by-two separates founders along two dimensions: exceptional versus not exceptional, and easy versus not easy to get along with. Botha says Sequoia historically made money in the exceptional, not-so-easy quadrant. The proposed mechanism is not that unpleasantness creates success. Rather, founders who refuse to accept the world as it is often push back strongly when advice conflicts with the change they are pursuing. The matrix makes an investment team's observed outcome pattern explicit and warns against selecting merely comfortable relationships. Applied carefully, it requires evidence of outlier capability and productive insistence while preserving a separate boundary against destructive conduct. It is a historical decision lens, not a license to treat every difficult personality as an exceptional founder.
Origin
Sequoia founder Don Valentine gave Botha the matrix soon after Botha joined the firm and asked him to discover which quadrant produced returns.
Core principles
- 01Outlier outcomes depend on exceptional founders
- 02People who challenge the status quo may also challenge their partners
- 03Easy collaboration is not the same as exceptional ability
- 04A matrix makes an implicit preference visible
How to run it
- 1
Define exceptional
Specify the evidence that would distinguish an outlier founder from a merely investable one. Use demonstrated insight, ability, ambition, or problem-solving rather than charisma alone.
Pro tip Anchor the standard to the outcomes of previous founders in the same decision context.
Watch out Confidence and exceptional ability are not interchangeable.
- 2
Assess collaboration
Observe whether the founder is easy or difficult to work with, especially under disagreement. Identify whether pushback protects a coherent mission or simply damages relationships.
Pro tip Use real decision conflicts rather than social smoothness as evidence.
Watch out Do not romanticize abusive behavior as founder intensity.
- 3
Place the quadrant
Classify the founder on both dimensions rather than averaging them into one vague impression. State what evidence supports each placement.
Pro tip Have reviewers classify independently before discussing the result.
Watch out A neat quadrant can conceal weak or biased evidence.
- 4
Compare with outcomes
Review which quadrants historically produced the results relevant to the organization. Use that pattern to challenge comfort-driven selection while still judging the individual case.
Pro tip Revisit the pattern as the portfolio and team change.
Watch out Historical correlation does not guarantee the next founder's success.
In the wild
The founders worked on different Stanford networks and could not send electronic mail across campus. Their unwillingness to accept the inconvenience led them to connect the networks, illustrating the kind of frustration-driven action Botha associates with founders who challenge the world as it is.
→ A mundane boundary became the founding inspiration for Cisco.
Common mistakes
Selecting for pleasantness
An easy meeting can bias a reviewer toward a founder without the exceptional qualities required for an outlier outcome.
Excusing destructive conduct
The matrix describes an observed pattern; it does not make every form of difficult behavior productive or acceptable.
Is it for you?
Best for
It is best for teams reviewing founder patterns across a portfolio of high-risk, high-upside ventures.
Not ideal for
It is not ideal when used to excuse abuse, dishonesty, or behavior that makes a working relationship impossible.
From the transcript
“there's a two by two metrics of people we get to invest in exceptional not exceptional uh easy to get along with not so easy…”
“it's you know exceptional not so easy to give along with”
“founders are these people who don't take no you know they don't accept the way the world is they want to change it”
From the episode
#618: Roelof Botha — Investing with the Best, Ulysses Pacts, The Magic of Founder-Problem Fit, How to Use Pre-Mortems and Pre-Parades, Learning from Crucible Moments, and Daring to Dream
Roelof Botha