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An Entrepreneur's Guide to Personal Grooming

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Soon after I quit the corporate grind and started my own consulting firm, I stopped by my old company to have lunch with the CEO. He walked into the lobby, looked me up and down, and said, “You look like a rock star.”

And, no, I don’t think he intended it as a compliment.

A few weeks later I ran into another former boss – the chief executive of a Fortune 500 company – who took one look at me and remarked, “Tobak, you need to stand closer to your razor.”

Again with the comments about my grubby work-at-home look.

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Did I take the feedback about my personal grooming to heart? I’d have to answer that “yes and no.” While my days are mostly spent where nobody can see me but my wife, my dogs, and a few rabbits – none of whom give a damn how I look … or smell, for that matter – I do clean up for the occasional business meeting.   

Having been at this for more than a decade now, I’ve pretty much mastered all the pitfalls of the work-at-home gig. And that includes what most people – unlike my former bosses – would be too polite or find too awkward to say to your grubby face.

Fortunately for you, there isn’t a polite bone in my body.

So, if you’re an entrepreneur or small business owner, work from home, have bills to pay, and can’t exactly afford to lose any clients, associates or connections because you left the house looking and smelling like a homeless person, here are five essential personal grooming tips.

Try showering. You won’t melt.  What you do is head into the bathroom – it’s the one right next to the room where you sleep – and look for a metal thing coming out of the wall about a foot or so higher than your head. It’s a bit tricky but, if you can figure out how, you can get water to come out of it. Now stick your head under there and … what’s that? No, dummy, you get dressed afterwards.

They can still see you on , you know. You know those early morning Skype calls with associates on the east coast or in ? I once sat down in front of the computer in my PJs with my hair looking like what my wife likes to call devil horns and nearly fell out of my chair when I saw my image in the little popup window. Oh yes I did.

Also, if you think you can get away with just a nice shirt over your holey old shorts, trust me, you can’t. At some point you’ll get up without thinking and, well, it won’t be pretty. 

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No, double-breasted suits are not back in style. I know, I have a closet full of old dress clothes, too. The problem is, when the dot-com bubble burst and all the money got sucked out of like the VCs turned on an enormous vacuum cleaner, all the designers got together to find a way to get entrepreneurs to spend what little they had left on clothes.

Every decade or so, take a trip to downtown and check out how people with real jobs look. If it feels like you’re in a science fiction movie, better get down to and drop a few bucks.   

Women dig the stubble. Top execs, not so much. While the two-day stubble look has taken off since I invented it 11 years ago, it doesn’t exactly reflect the image of a high-paid consultant to senior executives. So even if your wife loves it – or at least the look of it – I’d be willing to bet she loves the big bucks even more. Be on the safe side and shave until after you’ve won the business and proven yourself.

Go to annually, whether you need to or not. If the last time you visited a pharmacy was sometime during the Clinton administration, better prepare yourself – it might be overwhelming to see that many cleaning products all in one place. If you’ve forgotten what shampoo and deodorant look like, just ask someone with a nametag to help you. They deal with that sort of thing all the time.  

Incidentally, I have to apologize to all the work-from-home women out there, but for obvious reasons, I’m in no position to advise you on this sort of thing. But if there’s a guy in your life, you might want to forward this to him. I mean, somebody’s got to do it and, if not you, then who?

Related: The Key to Success? Relationships.


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