Talking People Out of Being Entrepreneurs

In the last few months, there have been a number of people whom I’ve tried to talk out of being entrepreneurs. I tell them it’s really a test to see if, after hearing about how hard it is, whether or not they actually still want to do it.
There are many who are newcomers to entrepreneurism. I think this is great. But I think most of the newcomers underestimate what it takes to start a company and make it successful.
So I let it all out. I tell them how it requires some serious soul searching about what kind of person they are. You have to be natural risk taker. You must be willing to throw all caution to the wind, because you never know what’s going to happen. You must be willing to throw away all levels of comfort in hopes of some huge gain later on. Are you OK with leaving your current job and its consistent pay, health insurance, and sense of direction in your life for a lot lower pay and the chaos that accompanies typical startups?
I talk about the time commitment. I talk about my early Yahoo days when there were just a bunch of us, and we worked our tail off for years. I talk about the long hours we spent building Yahoo back in the day, the stress, the do-everything-yourself mentality and the chaos of not knowing what’s coming next. I tell them about the fact that relationships have broken up due to training for Ironman, which even at its peak, doesn’t equate to time commitment spent at a startup and for a longer period of time. I go through the inevitable ups and downs that come with relationships and families of entrepreneurs; it’s not an easy place to be when your work and family demands collide.
I make them take a hard look at themselves, and I also gauge their reaction to what I say. I can see it in their eyes and in their replies if they are unwilling to give it up. My intuition is running high in sensitivity as I sense whether or not they have what it takes to go the extra distance to be a successful entrepreneur.
Don’t get me wrong; I am not judging what’s good or bad, but only what’s appropriate. I am not making a judgement call on whether you’re a good or bad person if you have or do not have what it takes to be an entrepreneur. For some people, it’s just not the right path to take. Yes it’s disappointing, but I think we need to be realistic that entrepreneurism isn’t for everyone. Or perhaps your life stage is now not the right time for a startup – for example, having a family and/or dependents, and/or a lifestyle which requires steady income may not make it appropriate for you to jump into a startup.
This is really important. We investors are betting on you to take our money and build something big with it. We are looking for those who are willing to do anything it takes to make something successful so that we all win, and that means sometimes driving yourself into the dirt and dealing with the stress of knowing that your bank account is about to run out and that if you don’t do something fast/creative/better, you’ll not be able to feed yourself or have a roof over your head anymore. This kind of passion/adaptability/drive for building a great company is what we’re looking for.
If you’re going to quit as soon as the risk is too high for your own personal livelihood, then it’s best that we just don’t start. It’s not positive for either of us. Find an occupation that allows you to live the life you want, at the stage you’re at now and be happy about that. Don’t try to start a company on the assumption that you’re going to just have the same kind of life you did when you worked at a bigger company.
One of the big problems I’ve seen over the last 3 years of angel investing and with entrepreneurs is that they will raise money and then compensation goes to near market levels for the people in the startup. They think that they can be in a startup and have their old lifestyle not be threatened. The reality is that startups are not a place where lifestyle can be guaranteed. This ranges from the “working lean and mean” philosophy (how can you pay yourselves market rates and still be lean?) to execution speed (you can’t work at speeds seen in large organizations; you’ll get crushed by other startups) to just the simple fact that the risk of failure is tremendous (you don’t get the comfort of stability in a startup that you would get at a larger more established company; that’s the price you pay for constant salary versus the chaos of a startup).
So if you pass my test, which is, after my whole tirade about the risks of startups and the downsides of what it’s like to be an entrepreneur, you are still fired up about being one, then more power to you. Let’s take this conversation further. But I am getting better at spotting hesitation, fear, and reluctance after hearing my speech. So let’s not kid ourselves in being somebody we’re not.
It’s sexy being an entrepreneur. The rewards are great. The upsides are what everyone sees, and nobody sees the downsides. Dealing with the downsides is where the rubber meets the road and where you’ll be tested sorely on whether or not you are a great entrepreneur. But if you’re not entrepreneur material, you’re not and that’s that, whether it’s your personality, life stage, or otherwise. You’re not a bad person; it’s just not for you and we should all just realize this, and not fool ourselves into thinking otherwise.