Why Studying Steve Jobs (and Other Founders) Can Lead to Failure and Depression

Counterintuitively, it can reduce your likelihood of success

Hi Founders 👋

Martin here, welcome to Issue #2 of Founders’ Hustle 👊

Today I’m tackling a super important topic — founder psychology.

It’s often overlooked or awkwardly ignored in the startup ecosystem like some kind of inconvenient issue. For that reason I intend to circle back to it regularly in this newsletter. If you have a specific subject you’d like to surface within this topic or would like to add anything please feel free to reach out.

Now, lets talk about founder idolisation. You know, those ‘superstar founders’ that are idolised not just by the tech community but mainstream society.

The press can’t stop talking about them. They’re better known than most world leaders. Their products changed the world. A Hollywood film has been made about their origin story.

Everyone obsesses over their behaviour and craves to distill their habits and methodologies into a replicable formula that can be utilised as a competitive advantage.

Sometimes they’re even pseudo-worshipped — I’m thinking of you, Steve.  👀

The media about these superstar founders is particularly alluring. I’m personally a bigger sucker for the films — The Aviator, The Social Network, Steve Jobs (‘Danny Boyle version’), Jobs (‘Ashton Kutcher version’), The Founder etc.

Even though it’s widely known the accuracy of these films can vary significantly from reality, they suck you in. They’re a biased lense into the success of these superstar founders at the most crucial time — the beginning.

As a founder in particular, it’s too hard to resist taking a peak despite the inaccuracies and exaggerations.

I also really love biographies, interviews, articles and anything else that you can really sink your teeth into. Consuming books written by (or about) some of the most successful founders of the 20th century has been significant to my own personal development.

Despite the bias, for many (including myself), this collective media is inspiring, motivating, insightful and helpful. Particularly if the information is balanced, weighted and verified appropriately.

However, doing this can make it counterproductive and even harmful — contributing towards depression and failure.

A ‘psychological bug’

As humans, learning about successful folks in a field we are passionate about can lead to skillset and achievement benchmarking and a sensation of underachievement, failure and ineptness.

This is the basis of social comparison theory - a theory initially proposed by social psychologist Leon Festinger in the 1950s.

In a nutshell:

Social comparison theory is the idea that individuals determine their own social and personal worth based on how they stack up against others.

A lot of the time this is helpful for humans since it spurs us on and makes us try harder and achieve more. It’s evolutionary helpful:

Social comparison can be highly beneficial when people use social networks to [compare upwards] and push themselves.

For example:

  • A friend who just won an award.

  • Your competition that just closed a VC round.

  • The person next to you at the gym running 2x faster on the treadmill.

Witnessing all of this can push you to try harder and achieve more than if the competition didn’t exist. The goals you set in this context might be inspired by your peers and as such, they’re broadly achievable.

This can be a positive force but there’s also an ugly element embedded within social comparison theory — what I call a ‘psychological bug’, which is the ‘paragon effect’. 

This is when, rather than using your own network and a broader set of people collectively as a benchmark to measure your own success, you use just one individual or a handful of people who possess the perfect example of a particular quality you find desirable.

These individuals are paragons. They’re rarely within your network. They’re elite of the elite achievers. They’re idolised. They’re inimitable.

This skews your basis for comparison to an impossibly high and uniquely distinct standard. For example, if you’re a founder and you suffered from the ‘paragon effect’ with Steve Jobs your measure of success is Steve Jobs.

Your measure of success would be his intellect. His incredible storytelling. His youth when founding Apple. His unique experiences. His vision. His charisma. His impact on society. His fortune. His legacy.

That’s a tall order.

You might experience a sustained sensation of underachievement, failure and ineptness — which can be a contributing factor towards depression.

Whilst that can be motivational in short bursts, over the long haul it can lead to a bad place. Because, there’s only one Steve Jobs. There’s only one you. We’re all on our own journey.

And, Steve Jobs is just an example here. I picked him because, for founders, he’s an obvious choice. A paragon can be anyone perceived to be a perfect example of a quality any individual finds attractive — it’s subjective.

It can also escalate to the point where you use a different paragon for each quality you want to emulate. The wealth of Jeff Bezos. The cult of Steve Jobs. The philanthropy of Bill Gates. The genius of Nikola Tesla. The ‘Iron Man’ persona of Elon Musk.

This creates an even more unachievable superhuman character goal to live up to in your mind. Ultimately, it can lead to a never ending mission of unfulfilled self-actualisation.

This can contribute to sustained unhappiness and frustration, altering your behaviour negatively over the long term and reducing your productivity levels. Perhaps, even lead to giving up.

Balance is key

I’m a big believer of studying and learning from superstar founders. But, in a healthy and constructive way. It’s totally achievable and many founders do it successfully.

To action this sustainably, my suggestion is to consume media on superstar founders but try to balance it across a wide dataset — your network, extended network, a broader set of elites and successful people on different levels. Don’t allow any one person to dominate your learnings or benchmarks for success.

The key is to consciously assess your social comparison methodology regularly. Verify that you’re not suffering from the paragon effect on these occasions.

Admittedly, this is easier said than done because as humans our social comparison framework is partly subconscious and so habitual that we don’t even realise we’re doing it.

So, try to do this more consciously and actively by identifying and breaking down what your social benchmarks for success are and how they are defined. And, try to be specific.


  • Bootstrap a unicorn in X years.

  • Raise a Series A funding round from Y top tier VC.

  • Build product A for market niche B that captures 20% of the value in market niche B within five years.

If they are not specific it can be an indication that your social benchmark is an intangible and unachievable goal routed around one person. Like a character construct or unrepeatable set of events that you will forever chase instead of a measurable metric or achievable result.

Examples with the paragon effect:

  • Become a global consumer tech icon with a cult following, like Steve Jobs.

  • Incept a platform disruption shift, like Steve Jobs did from PC to smartphone.

  • Change the way everyday consumers use technology, like Steve Jobs.

None of the above are actually achievable because they’re ambiguous and routed in a unique and personal story.

Once you have identified what your social benchmarks are, query if they are heavily biased towards one person or a small group of people. Dig deep.

If they are, don’t fret, you can use this as a basis to recalibrate your own social comparison methodology. One that creates the optimum balance of sustained competitive drive and achievable self-actualisation and satisfaction. Incorporate more people with repeatable comparisons.

It will take effort and trial and error to do this well. Filtering with too fewer people leads to chasing an unattainable goal. Filtering with too many makes goals too accessible and drives down competitiveness.

The key takeaway here is we’re all on our own journey. Learn from paragons but infuse insights from them with a broader dataset to calibrate your own distinctive social benchmarking framework. Otherwise, it can be destructive.

“Your time is limited, so don’t waste it living someone else’s life.” —Steve Jobs

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Image credits

AB / Unsplash

Halacious / Unspash

Jared Rice / Unsplash