Inside a CEO’s drawers

Generally it’s a worry when an investor wants to look over the CEO’s shoulder, calling and emailing all the time: “how’s it going?”, “did you close any sales this week?”, “what’s the status of the top 25 product bugs?” This is known as getting in your CEO’s pants, meaning being so close as to be very uncomfortable and a little inappropriate (and, heaven forbid, nothing more than that).

Sometimes, however, there is a moment when getting in a CEO’s drawers is quite illuminating, and by drawers I mean office furniture … not clothing!


Take a look at this picture I took of the contents of the top drawer of a well-respected startup CEO in the Boston area. What does it teach us about the life of a CEO?

  • Antacid – largest and most obvious item … hmmm, stressful job?
  • Altoids and Orbit Gum – keep that breath fresh while talking, talking, talking to customers, employees, investors, partners.
  • USB cable – “tech credentials”.
  • Painkillers – THREE kinds! – hmmm, stress gives you headaches?
  • Energizer batteries – I hope this CEO is not taking this “high energy” food kick to extremes.
  • Pens – for when the PC fails and you need to write down that number.
  • Tissues – allergies, or so much stress a good cry can sometimes help?
  • Lubriderm – perhaps those vulture capitalists sometimes look like alligators.

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