Deciding to Start a Company
Deciding to start a company should not be taken lightly. With your time, money, energy, relationships and even health at stake, you should be well aware of the journey ahead of you. You should also consider whether it is best that you use the upcoming timeframe to work and learn the ropes under another founder and managing team so that you can be better prepared to start a company at a later time.
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There’s one question to ask yourself periodically, especially when considering a new assignment over an external opportunity, and that question is: Imagine you were at a different job you loved and a recruiter from [Google/ Apple/ Facebook] called you to offer you your current job at [Google/ Apple/ Facebook], would you chase it? Or in other words, would you re-apply today for the job you currently have? If you answer “no, I wouldn’t fight hard for the job I have” then you owe it to yourself to find something that you can be excited about.
You usually hear about people wanting to start companies because they have a problem they want solve or think they have some unique insight that might result in bags of cash. I think there is another reason that is spoken of less frequently. When people would tell me how hard it was to build a company a certain itch would arise that made me wonder if I had what it took to start my own. Ultimately, I think it stems back to the fact that we as humans compare ourselves and abilties to our peers to seek external validation. I don’t think this motivation alone is the right ingredient for building a successful company. However, I do think its important to recognize its existence and be aware of how it affects our professional decision making.
I had a really interesting conversation about why we want to be entrepreneurs a few weeks back that made me take a good hard look in the mirror. I think a lot of people say they want to be entrepreneurs without ever really taking a good hard look their core motivations, myself included. The friend I spoke with said that his main motivation to take the entrepreneurial leap, among others, was to swing for the fences with the chance that he’d never have to worry about money again. This friend of mine choose to take a job that would better prepare himself to become an entrepreneur than get in early on a later stage startup. He knew the later stage startup would be a huge success, but his ultimate goal was to build his own successful companies. He opted to turn down the promising opportunity for one that he thought would better prepare him to become a successful entrepreneur.
Seeing how entrepreneurs handled adversity and difficult decisions tells me a lot about who I’m going to be working with if I invest. I learn much from hearing whether they have humility, understanding what they learned from their failure (or success), gauging the speed of decision-making and willingness to admit when they were wrong. I also look to see whether they can make the really difficult decisions (like firing all of your friends – this is no fun.)
I often have career discussions with entrepreneurs – both young and more mature – whether they should join company “X” or not. I usually pull the old trick of answering a question with a question. My reply is usually, “is it time for you to earn or to learn?”