The psychology of successful bootstrappers

the psychology of successful bootstrappersI am curious about how the people who bootstrap software businesses are different to the general population, and to each other. I investigated this using a standard (‘big 5’) personality test. I think the results make for interesting reading.

I asked a number of software company founders to complete an online personality test and send me their results. 18 of them did (19 including me). You have probably heard of some of them, however I promised anonymity. We are all founders of bootstrapped (i.e. not VC funded) software product companies and have been involved in programming a significant portion of our products. Most of us are solo founders. Some of us (including myself) are lifestyle programmers, others have employees. We are all successful to the extent that we make a living from our software product sales. None of us are billionaires (Bill Gates probably wouldn’t return my email).

The test measures personality across 5 major axes of personality identified by psychologists:

  • Extraversion (outgoing/energetic vs. solitary/reserved) – how much you derive satisfaction from interacting with other people.
  • Conscientiousness (efficient/organized vs. easy-going/careless) – how careful and orderly you are.
  • Neuroticism (sensitive/nervous vs. secure/confident) – how much you tend to experience negative emotions.
  • Agreeableness (friendly/compassionate vs. analytical/detached) – how much you like and try to please others.
  • Openness (inventive/curious vs. consistent/cautious) – how much you seek out new experiences.

See Wikipedia for more details.

For each personality axis I have created a histogram of the results, showing how many founders fit in each 10% ‘bin’ compared to the general population. For example, for extraversion: 0 bootstrappers were in the 1-10 percentile (i.e. least extrovert 10%) of the general population, 1 founder was in the 11-20 percentile, 2 were in the 21-30 percentile etc.


Extraversion Conscientiousness Neuroticism Agreeableness Openness
average (mean) 59.9 61.7 37.6 48.3 50.3
standard deviation 23.0 21.9 23.1 21.1 23.2

If bootstrappers were like the general population we would expect each bar to be the same height, with a bit of random variation, and the average score to be 50. Clearly this is not the case.

We are more extrovert on average than the general population. Although programming is stereotypically a profession for introverts and quite a few of us work alone, you need to get yourself noticed and interact with customers and partners to be a successful bootstrapper.

We are more conscientious on average than the general population. Shipping a software product requires a lot of attention to detail.

We are less neurotic on average than the general population. You need a some self belief and a thick skin to weather the ups and downs of being a bootstrapper.

We are about average for agreeableness. However the scores are not evenly distributed. Only 1 scored above the 70 percentile. Perhaps being too ready to please, rather than following your own vision, is a handicap for bootstrappers.

We are about average for openness. But the scores are clumped around the centre. Initially I was a bit surprised by this result. I expected bootstrappers to be inventive/ideas people and to score well above average. But perhaps the people who score very highly on openness are easily distracted (squirrel!), and never get anything finished.

The 5 personality traits are supposed to be orthogonal (not correlated). Picking some random pairs of traits and drawing scatter plots, that does indeed appear to be the case. For example extraversion doesn’t appear to be correlated with conscientiousness:

extroversions vs conscientiousnessI am aware that this survey suffers from some shortcomings:

  • The test is fairly simplistic. It doesn’t begin to capture what unique and precious little snowflakes we all are. However I don’t think I would have any results at all if I asked people to complete a massive survey. We are busy people.
  • Any survey suffers from selection bias. I am more likely to know other founders who are extroverts (the introverts probably go to less conferences). It is also likely that the people who responded were more conscientious and agreeable than those that didn’t!
  • 19 is a small sample size.

Correlation doesn’t imply causation. So these results don’t prove that high levels of conscientiousness and extraversion and low levels of neuroticism make you proportionally more likely to succeed at bootstrapping a software company. But, given that personality is considered fairly stable over time, it seems unlikely that the success caused the personality traits. However both could be correlated to some underlying factor, e.g. these traits could conceivably make you more likely to try starting a software business, but no more likely to succeed. Or the correlations could conceivably be a statistical fluke. I leave it as an exercise for an interested reader to work out the exact level of statistical significance of these results. It would be interesting to compare these results with those who tried to bootstrap business, but failed. However such data might not be easy to come by.

Given what I know about the trials of starting your own software business I think an above average level of conscientiousness and extraversion and a low level of neuroticism are a real asset. However it is also clear that the personalities of individual founders vary a lot. So don’t be disheartened if you don’t fit this profile. There are successful bootstrappers who don’t fit the profile. Personality is not destiny. And you can always partner with or employ someone who has complementary personality traits. But if you are a slap-dash, neurotic, who doesn’t like talking to other people, perhaps bootstrapping a software company isn’t for you. A career in government funded IT projects might be more suitable.

I sent a draft of this post to Dr Sherry Walling for feedback. Sherry is particularly well qualified to comment as she is both an adjunct Professor of Psychology and married to well know bootstrapper/micropreneur Rob Walling. Her response (paraphrased a bit) was:

“Your standard deviations are quite large which indicates that there is quite a lot of variability in your data. You would much rather have standard deviations between 0-10 when working with this kind of scale.

From my perspective, the only domain where I would expect significant difference is Conscientiousness. Conscientiousness is an essential bootstrapper trait. I am not sure how a solo founder could be successful if he/she is not naturally conscientious.

There are so many ways to be a successful bootstrapper. A neurotic person can fuel his sensitivity to negative emotions into hard work. A less neurotic person may not have enough anxiety to get up early and get to work. On the other hand too much neuroticism can be very debilitating. I don’t think there is a formula. The combination of factors could vary tremendously with each person, but conscientiousness is the one that seems essential.”

If you want to do your own analysis, the anonymised results are available to download as a CSV file here.

Many thanks to everyone who took part in the test.

You can do the test yourself. You don’t have to give your email address or answer the additional questions at the end. How do you compare?

5 thoughts on “The psychology of successful bootstrappers

  1. Simeon Pilgrim

    Interesting… E 83, C 3, N 75, A 26, O 47, not what I was expecting, but I tried to not thinking where the question was going, and just shot from the hip… For the record, not a founder, I want to… just not found a ‘thing’

  2. Gene Wirchenko

    Not that useful. Note that all of the mean values are within one standard deviation of 50. Three are within 1/2 SD; the other two are within 0.54 SD. Consequently, this does not state much.

  3. Andy Brice Post author

    According to my calculations, looking at the number of scores above or below the 50 percentile the sampled population is:

    -above average extroversion at 82% confidence
    -above average conscientiousness at 92% confidence
    -below average neuroticism at 99% confidence

    95% confidence is usually considered strong enough.

  4. Mohamad El-Bawab

    In my opinion, people don’t tend to describe themselves accurately as they rather to appear humble and more mainstream-like. I am curious to see what others would describe the bootstrappers in terms of those same dimensions.

  5. Andy

    Great post. My own opinion based on my observation of others is that the conscientiousness / attention to detail is absolutely vital.

    I’ve known academics who have started spin-off companies without realizing that having the good idea is only the beginning. Dealing with irate clients, the discipline of working to agreed specifications and standards, going the extra mile, getting up early to guarantee appointments are made and so on and so on…

    The laissez faire approach may be fine if it’s just a research tool or a proof of concept, but in the real world basing it upon sound business principles is inescapable.

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