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Diary of a CEO · 2021-03-01 · 52m

Extremely Honest Q&A | The Diary Of A CEO | E70

Stephen Bartlett answers fan-submitted questions with brutally honest takes on meaning, money, imposter syndrome, sales, and his weaknesses.

Extremely Honest Q&A | The Diary Of A CEO | E70
The guest

Stephen Bartlett — Entrepreneur, co-founder of Social Chain, and host of The Diary Of A CEO podcast.

The gist

In this solo Q&A episode (E70), Stephen Bartlett answers questions submitted by his audience, promising brutally honest answers. He covers lessons from the pandemic, how to maximize earning potential by moving skills to higher-value markets, dealing with imposter syndrome, doing things you don't want to do, and the meaning of life. He shares personal admissions about his greatest weaknesses, including neglecting family, self-centeredness in relationships, and growing impatience that borders on rudeness. He also discusses the loss of appreciation that comes with wealth (hedonistic adaptation) and how to handle ridicule when posting your business publicly.

Big reveals

  • Bartlett says the same set of skills can earn 10-50x more simply by moving to a market where those skills are rarer and more valued, comparing it to a company being worth 4x more on the NYSE than a small German exchange.
  • He raised investment around 20 times and credits cold-call telesales call-center work (starting at 16 selling double glazing) as the most valuable training of his life.
  • He admits his greatest weaknesses: not calling his parents enough, being self-centered and unwilling to compromise in relationships.
  • He confesses that as a busy entrepreneur he has become so impatient that simple questions from his PA feel like 'an irritant.'
  • He recounts being publicly snubbed by the 'Man vs Food' host in business class, which taught him every interaction matters.
  • He confesses he misses being at the bottom of the mountain and that achieving his goals removed the excitement, requiring ever-bigger goals to feel hunger.
  • An unnamed billionaire friend confided he wished his life were simpler and that he didn't have so much ambition.

Things worth remembering

  • Bartlett frames responses to chaos around three principles: acceptance, optimism, and action.
  • He describes the 'second L' concept: the first loss is involuntary, but choosing denial, pessimism and inaction is a voluntary second loss.
  • Elon Musk reportedly became depressed pondering life's meaning as a child until reading Hitchhiker's Guide to the Galaxy.
  • The 'Rat Park' study showed rats in barren cages became drug addicts while rats in a stimulating environment avoided heroin.
  • He cites Johann Hari's work arguing depression often stems from lost meaning and trauma rather than a chemical imbalance.
  • On weekends Bartlett combats loneliness by learning to DJ via weekly Zoom lessons and reading philosophy books.
  • He worked in roughly 12 different telesales call centers, quitting after big bonus runs to fund his business attempts.
  • His business partner Dom faced snide 'banter' from hometown friends when Social Chain started, illustrating envy from people who can relate to you.
  • He references Spotify founder Daniel Ek having an existential crisis after getting rich and realizing money 'wasn't it.'

Recommended in this episode

Books, products and media the guest or host genuinely endorsed here — with the buy link.

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Guest’s ownBook

Happy Sexy Millionaire

Stephen Bartlett

“it's a book called happy sexy millionaire which is authored by me” — Stephen Bartlett 00:50:03
Find it on Amazon