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5 Dark Secrets of Entrepreneurship: What (Almost) No One Tells You About Starting Your Own Company

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Before becoming an entrepreneur I worked with many of them closely for five years. I watched them start, grow, exit, ruin, and shut down their companies. You'd think there would be few things about starting a company that would surprise me. You would be wrong.

During my still-very-short tenure as an entrepreneur I've discovered many things that have surprised me. Here is my list of 5 Dark Secrets of Entrepreneurship. I'm sure it's not exhaustive.

1. An entrepreneur, you feel stupid much more often than you feel smart.

Most entrepreneurs I've met in my time as a VC were really smart. Not all had good business ideas or solid management skills, but they were sharp. At the risk of sounding self-indulgent, I think of myself as a generally smart person. And yet, as I've been working on launching my company, I've felt dumb and stupid more often than I care to share. I've made bad decisions, wrong choices that in retrospect seem so easy to have been avoided, and I've learned a great deal about things I thought I already knew a lot about. Entrepreneurship is all about trying and building new things. Regardless of how smart you might be, doing something completely new and making endless mistakes can be stupefying.

(Now, I'm no Marc Andreessen and perhaps after a few billion dollar companies under my belt I'd feel less stupid starting my next one, but I'm not sure. Maybe I'll email Marc to weigh in on this.)

2. Everyone is your greatest fan when you start, but support wears off quickly.

When I told friends and business contacts that I was starting my own company, the enthusiasm was overwhelming. It was like going from one cheer-on session to another, with tons of encouraging emails and calls sprinkled in between. It felt great and gave me a lot of confidence about what I was doing.

But this overwhelming support began to wear off as time went on. The big news about my new gig wasn't news anymore and support quickly turned into feedback. Feedback is great -- it's useful and necessary. But it came in heavy non-stop doses. EVERYONE I knew wanted to give me tips on everything from what our website should look like to how I should word our email newsletters. Emails that began with: "Hi, I was just checking out your site and wanted to give you some advice," became very frequent. I found myself with a strong urge for those great support-filled emails that flooded my inbox earlier on. As maybe too few entrepreneurs will tell you, we need as much cheerleading as we can get.

3. Regardless of your confidence level, you will often experience crises of confidence.

Most entrepreneurs I know are generally confident people. I don't think it's possible to take on the enormous amount of risk starting a company requires without being confident in your ability to overcome it. Apparently experts agree, which makes me even more confident in this assumption.

But being an entrepreneur involves consistently overcoming crises of confidence. You feel hopeless about making progress, you think your business is doomed, you think you've made the worst decisions ever. This is a crisis of confidence and you have to work very hard to overcome it. It's a horrible feeling.

4. Nothing is ever right on the first try.

Your website design needs to be re-done. You hired the wrong sales guy. You strategy is wrong. Your name is spelled wrong on your newly ordered business cards.

Nothing works on the first try and regardless of how much you expect this, you feel crushed when it happens and you think you'll get it right the second time around. Sometimes you do, but often you don't. Our company is four months old and we've redesigned the homepage twice, modified our focus, changed many of our tactical feature implementations. Intellectually, I knew this is part of the process -- everything is iterative and you learn only by doing. Emotionally this is rough because it often leads to #3.

5. You will take everything personally.

This morning an email came into the info box. It was from a woman who is married but chose not to have children. She spent three paragraphs writing about how prejudicial, judgmental, demeaning, biased, and damaging it was to create a site for professional moms (vs one for professional women). I read the email quickly and moved on to the next one. But it kept nagging me as I worked. I wanted to reply, to tell her the many reasons why I disagreed with her. I took it personally.

Now, some of you might want to dismiss this as a woman-thing, but don't. I've now met enough entrepreneurs who say this is true -- and they never admitted it to me until I became one of them.

What am I missing? Share your favorite dark secret of entrepreneurship in the comments.