You Aren’t Alone: A Great Post on the Struggles of Entrepreneurs

Glen Kelman has written a guest post at Guy Kawasaki's blog called On the Other Hand: The Flip Side of Entrepreneurship. Glen discusses the recent trend towards easy entrepreneurship, with sites like HotOrNot and PlentyofFish taking off and making millions for the founders who work just a few hours a day, Glen re-visits the idea that building a new company is really pretty hard, and that he actually likes it that way.

Lately I've been thinking how hard, not how easy, it is to build a new company. Hard has gone out of fashion. Like college students bragging about how they barely studied, start-ups today take care to project a sense of ease. Wherever I've worked, we've secretly felt just the opposite. We're assailed by doubts, mortified by our own shortcomings, surrounded by freaks, testy over silly details. Trying to be like James or Markus has only been counterproductive.

And now, having been through a few startups, I'm not even sure I'd want it to be that easy. Working two hours a day on my own wasn't my goal when I came to Silicon Valley. Does anybody remember the old video of Steve Jobs launching the Mac? He had tears in his eyes. And even though Jobs is Jobs and I am nobody, I knew how he felt. I'd had the same reaction-absurdly-to portal software and more recently to a Redfin, a fledgling real estate website.

Assailed by doubts? Mortified by our own shortcomings? Surrounded by freaks? Testy over silly details? check. check. check. check.

Standardized tests put me in the 99th percentile for IQ. I have a MBA. I read about and study business compulsively. You would think I would have more confidence in my business abilities, and yet starting a new business routinely makes me feel like an idiot. Mistakes occur on a regular basis. Money gets wasted. If you have been through it, you understand why it doesn't appeal to normal people. It will make a mess out of a person with fragile self-confidence. It's particularly painful and humbling when you realize that your idea isn't going to work and you have to shut it down or change it significantly. The only way I've learned to deal with it is to adopt this zen-like attitude that it's just a path I'm on and I'll put one foot in front of the other and do the best I can.

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But on the flip side, if you like solving problems, there isn't a better place to be in the world of business. Startups, even as just part-time side gigs, are full of challenging problems that push the limits of your thinking. Solving them gives you a sense of satisfaction that just isn't matched by most other work environments.

A week ago, Andy Swan, co-founder of Mytrade, wrote about his desire to blow a hole through the heart of Yahoo finance. Most people would probably say Andy is nuts to take on such a challenge, and doomed to failure against a company with such massive resources. But a handful of you weirdos out there will read that and say "wow, that sounds like fun." Day to day, the people you deal with don't understand you, but read Glen's post and you will realize you have kindred spirits.