An Investor’s View: Confidence and Doubt in Founders

A brief observation about two apparently opposing mindsets in some successful founders.

Channel
20VC with Harry Stebbings
Published
Mar 17, 2026
Video
0:33
Read
1 min
Original
English
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SUMMARY

In 30 seconds

An investor says some successful founders they backed combine strong confidence in their abilities with doubt about meeting their own ambitions. The clip offers an anecdotal observation.

  1. 1A personal patternThe claim is based on the speaker’s experience with selected founders.
  2. 2Confidence in abilityThe speaker describes a strong belief in personal capability.
  3. 3Doubt about outcomesThose founders may still question whether they can meet their ambitions.

Takeaways

  1. The speaker describes a pattern in selected founders, not a universal rule.
  2. Confidence and doubt can coexist.
  3. A belief in potential differs from certainty about outcomes.
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01

An investor’s observation

An investor describes a pattern they believe they have seen among some successful founders they backed: holding confidence and self-doubt at the same time. This is a personal observation, not a tested rule for every founder.

An investor describes a pattern they believe they have seen among some successful founders they backed: holding confidence and self-doubt at the same time. This is a personal observation, not a tested rule for every founder.

02

Confidence

The speaker says these founders believe strongly in their own ability and may regard themselves as unusually capable. Such confidence can influence how ambitiously they set goals.

The speaker says these founders believe strongly in their own ability and may regard themselves as unusually capable. Such confidence can influence how ambitiously they set goals.

03

Self-doubt

At the same time, the speaker says they question whether they can meet their own expectations. The proposed combination is conviction about potential alongside uncertainty about realizing it.

At the same time, the speaker says they question whether they can meet their own expectations. The proposed combination is conviction about potential alongside uncertainty about realizing it.

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