5 Dark Secrets: What (Almost) No One Tells You About Starting Your Own Company
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.
August 10, 2007 at 1:17 am
Failure is part of the learning process unless you quit
I left Apple so that my wife and I could start our own business. A year and a half later I went back to work in the cubicle nation. We’d blown through a lot of money and didn’t have a lot of tangible goods to show for it. I went through a period when I felt like a failure. I felt stupid.
“What the hell was I thinking, that I could do something like that??”
I would still like to build my own company. I’ve come to the realization that I’m only a failure if I quit trying. As Nataly said in one of her posts, if you’re starting a company, the odds say you’re going to fail. If you learn from your mistakes and keep trying the failures are learning experiences. It’s only when you give up trying that you become the failure.
Smittie
August 10, 2007 at 8:05 am
Smittie,
Not succeeding with your company after leaving a secure job feels horrible. But it’s the only way to learn so that you can try again. Luck and timing are big contributors to business success but you have to keep working hard to be there when they come your way.
Nataly
September 5, 2007 at 11:55 am
[...] 10. Believe in yourself. Entrepreneurship is lonely and frustrating. This is not something people talk about a lot because the thing that makes entrepreneurs successful is a crazy optimism that they can create something big from nothing. But underneath that optimism, is a fear that things will never work. [...]
September 5, 2007 at 5:20 pm
I’ve discovered your blog at a great time for me. I’ve just started my own blog, and the idea of working for myself has been bouncing around in my head for a few weeks now. I think that I’m lacking a certain experience, and want to make sure I have enough clients to bounce off of before I go anywhere, but I’m even thinking about company names. Have a look at my post: “Take What You’re Good at…”. Furthermore, I’m not ready to leave my salaried, experience-gaining job – I scored it less than a year ago.
I look forward to reading more on your entrepreneurial leap advice. Thanks!
September 20, 2007 at 2:05 pm
be bold and never never never give up, learn about wealth aquisition and have money work for you. read rich dad poor dad and you will make better decisions. thats my advice in a nutshell. and I started on my own 6 years ago and am still growing!!
September 27, 2007 at 10:59 am
I started my business (personal development coaching) almost 2 years ago now, and I can relate to everything that’s been said on this post! I started my company after hours while working in a law firm, and decided to make the jump to full-time entrepreneurship after about a year. Then eight months later, I went back to corporate America with my tail between my legs (sort of). The two biggest lessons I learned:
1) It’s okay to work at a day job until your business is consistently bringing in enough money for you to live on. I felt like a fraud by not “having faith” in my business enough to take a chance on it, so I left my secure paycheck much earlier than I should have. Now I realize that being a smart business person is more important (and will lead to more success) than proving myself to anyone else. I’m confident that someday I’ll once again be able to walk away from corporate life, but for now I’ve decided to let that happen when the time is right and just keep moving forward.
2) Take action! I love planning. I love dreaming up new ideas and new strategies for reaching my goals. But planning is a great way to avoid actually taking steps to build your business. Get outside of your comfort zone and just DO SOMETHING. Regardless of whether it leads to more clients or more money isn’t relevant - you’ll learn either way. Just get out there and make it happen. It won’t be perfect and you’ll make mistakes, but it’s worth it.
September 27, 2007 at 2:21 pm
Sarah - thanks so much for your comment and for sharing your experience. I know it must not have felt great going back to corporate, but it was probably a smart thing for you to do. You have to make sure that either your business brings you enough income or that you can have a dayjob while you build it up to that level - just having faith in it and starving is a really bad idea
November 26, 2007 at 3:29 pm
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