Chris Dixon once opined that there are two kinds of people in the world: those who have started a company, and those who have not. I do not take issue with this per se; on the surface, it is just another way to divide the human population into two groups. But I have some concerns about the particular way he characterizes entrepreneurship.
What troubles me most is the glorification of risk. Chris starts off on that theme by stating that, among other things, starting a company means “building an organization from a borrowed cubicle with credit card debt and nowhere to sleep except the office.” He then goes on to say, “The important distinction is whether you risked everything, [and] put your life on the line […] to make something new.”
Let me pause for a moment and state that I do not think Chris necessarily intended to glorify risk. More than likely, he was writing out of respect for entrepreneurs who struggled with unfortunate circumstances - so I think the message I am perceiving is not the one he intended to send. However, he might not realize how many people will see this post as an elaborated version of Nike’s “Just do it” campaign, and how they might consequently suffer.
What are the consequences of such a misreading? Obviously, a failed business can leave you in bankruptcy. But even if you avoid bankruptcy, a failed company can and very likely will damage your reputation and potential on the job market - and it is this rarely discussed phenomenon that I want to highlight.
In some cases, a failed company on your resume will not hurt you. Say you are a young programmer turned failed entrepreneur, and you have no dependents and nothing to lose. The hiring manager at Acme sees your application for their entry level programming job. Acme is planning on paying you about $50k, so while they hope you work out as a hire, they are not terribly concerned about it. If it is a big company, and you are able to demonstrate your skill, the hiring manager probably will not care all that much about your failed company and your bankruptcy (which will come up on the background check). And if Acme is a startup, you might even have an edge with your demonstrated entrepreneurial spirit.
The situation changes as you mature. Imagine that you have a decade of experience and, after your company fails, you apply for a senior job at Acme. Now the company is planning to pay you $150k, which means they expect to derive somewhere from $300k up to $1MM in revenue off of your work. At this level, they care a lot about whether or not this turns out to be a good hire. And suddenly, your failed company and bankruptcy do not look so good. You might hope that the company will respect your ability to take a risk and work hard, but with the amount of revenue pinned on your hire, what is really going to shine through is your demonstrated ability to lose money. And if you have a wife, 2 kids, and a mortgage, it will look even worse - now you also have a demonstrated willingness to put other people at risk. You better believe your resume is going to the bottom of the pile.
But what if your company does not fail? Suppose it just delivers middling results after 5 to 10 years and you decided to get out. (This happens way more often than you might think.) Regrettably, your situation is not much better than if your company folds completely. When someone hires you for $50k, it is not a huge deal if you leave after a year. But when they hire you for $150k, you typically need to stick around and be productive for at least 2 to 3 years before your employer has made a net-net profit. So a hiring manager sees your middling startup that you want to leave, and they wonder “How do I know this person really wants to work for me? What if they just get bored in a year and leave me in the lurch?” After all, the one thing all entrepreneurs really do have in common is a demonstrated preference for working for themselves.
These are the kinds of risks that bust up families and lead to suicides. And I am not speaking from theory here. I have personally witnessed families destroyed by bad businesses. And I have also done enough hiring to speak from experience about the aforementioned risks that entrepreneurship poses to your value on the job market. Suffice it to say, the consequences of playing and losing the startup lottery are very serious, and not in some abstract way. “Bouncing back” is rarely a very bouncy process. “Crawling back through a mile of mud and broken glass” would be a more apt term.
Chris Dixon is ferociously intelligent, and a very accomplished entrepreneur - and I believe that is why he is actually more risk adverse than you might think (or he might realize). Consider that he has three Ivy League degrees - including an MBA from Harvard Business School - and worked on Wall Street before entering startup-land. For those who might not know what that means, I will quote a friend who put it best: “I wish somebody told me when I was growing up that, with most jobs, the most you can make is hundreds of thousands of dollars, but with banking, the most you can make is millions upon millions of dollars.”
And Chris is not alone in this phenomenon. What do Bill Gates and Mark Zukerberg have in common? Surprisingly enough, they both attended Harvard, and only dropped out when their businesses started to take off. And even if those businesses had failed, they more than likely could have returned to Harvard and then proceeded to work on Wall Street. So they were a bit more able to soak up failure than average.
Likewise, look at the founders of Google, who studied at Stanford (which is very much Ivy-tier). Or look at Amazon’s founder Jeff Bezos, who graduated from Princeton and worked on Wall Street before founding the company for which he is now famous. Paul Graham has degrees from Cornell and Harvard. The list goes on. In fact, among the entrepreneurs I personally know who have had successful exits, every single one has either an Ivy league degree, or something comparable to that (e.g. Johns Hopkins). In all these cases, failure would hurt a lot less than for someone lacking the career benefits of an elite education.
I joined SkyLine when it was in startup mode. We really did work out of borrowed cubicles. The president and I both have the same humble alma mater - which is to say, he could not “fall back” on Ivy League credentials and a job on Wall Street. He also has nearly two decades of industry experience, and an extremely strong network. He put a ton of thought and preparation into the creation of SkyLine - in other words, he worked assiduously to reduce risk. Which is a very smart move, considering that if SkyLine had failed, the consequences for him - a family man - would have been tremendous.
I have a good friend who is a serious mountain climber. On those rare occasions where I brave the heights with him, I am struck by the intimate relationship he has with risk. The risks of climbing are palpable and lethal - if something goes wrong, you very well may die. He works meticulously to ratchet the risk level down to something manageable. And while he cannot completely eliminate or control that risk level, his efforts at risk-reduction have a great deal of influence over the likelihood of us living or dying that day.
Entrepreneurship is a lot like climbing. It can kill you. And just as the longest-lived climbers tend to be the ones who are the most calculating about reducing risk, so too are the most consistently successful entrepreneurs the ones who do not simply “take the plunge.” You can always throw caution to the wind and hope to be lucky - but nine times out of ten, you will be unlucky. And as another friend likes to say, “hope is not a method.”
Do not assume that everything will work out just because someone who has a lot of advantages in life told you so. Look before you leap, and look at who is leaping; if they are better equipped to take a fall, you might reconsider jumping after them. A failure that means nothing to them could mean everything to you, and that makes all the difference.