Pre-startup Advice

It occurred to me that trying to give startup advice to a founder is somewhat like coaching a marathon runner during the race: it’s not completely useless, but you’d want to start months or years earlier. Of course, as an investor you don’t have that luxury; you typically meet founders at mile 2 or 3 (e.g. YC, AngelList, demo days). This why there are so many startup advice posts by investors. I find it more interesting to think about those who want to start a startup, and who believe they’re ready for it. These are a few questions that I’d want a potential founder to ask him/herself:

  • Are you extremely competitive? The Silicon Valley startup ecosystem is about extreme competition. You will be competing for funding of course: an investor has limited money and attention. You’ll be competing for talent, press coverage and obviously for users/customers/eyeballs. And often it’s not a “you win some, you lose some” situation. For example, funding is usually “you lose lots, maybe you win one.”
  • Do you like selling? The above activities are not about building, they are about convincing others to give you something (money, resources, time, attention). If you like to build things but are terrible at selling, you’ll be competing against the best. It won’t be a fair fight.
  • Have you ever stuck with a multi-year goal despite unfavorable odds? Things like college obviously don’t count, because they are designed for your success. What does? Perhaps having worked thousands hours to get really good at something, especially if you didn’t seem particularly talented at it (a sport, a musical instrument).
  • Are you ok with doing mundane/boring stuff most of the time? Building a business is mostly boring work. Writing code is usually not boring (if you like it), but if you’re doing things right you won’t be coding for long. Or building hardware, or designing, or whatever. You’ll be attracting employees, keeping them excited, figuring out how to make money flow into your company (both through sales and investments). You’ll be dealing with lawyers, landlords, service providers. Giving presentations, tweeting, perhaps writing articles and/or interacting with the media. Your involvement with your product will decrease over time; if you really like product development (think Steve Jobs) you’ll either neglect other tasks or do it in your “free time.”

If not one of the potential founders is extremely competitive, I’d say don’t even bother. You’ll get crushed. If you’re lucky it will be quick and obvious, if not you won’t even know it for some time. Maybe you can learn to be competitive, but I have my doubts.

If you don’t like selling, see if you can force yourself to do it for a while. At the very least you must be decent at it, and not hate it. If you can’t or won’t… good luck.

If you haven’t done anything really hard that took years, why is that? If you’ve given up on too many things, that’s a bad sign. If you’ve accomplished something significant but it did not seem that hard, you have hope. Be honest with yourself regarding your ability to deal with an adverse situation for a long period of time. This one is hard to predict, so you may have to take a risk and see.

Do you really, really like coding? As in, is it really important for you to get better at building things, to hone your craft? That’s something to overcome. Startups are about getting people to use your stuff and eventually paying you by any means necessary. Nobody cares if your service or product is powered by beautiful code, minimum-wage employees, magic or impeccably logical Vulcans. Many aspects of your company will be barely good enough because you’ll be operating at your limits. If your software (or in general whatever is under the hood) is too good, it probably means you are sacrificing aspects that you can’t afford. Worse, you don’t even know it because you don’t get feedback from users who don’t exist, or from investors who rolled their eyes after you left the room.

The reason most of us only hear about the interesting aspects of startups is obvious: they make for good entertainment. Boring, mundane work is not news. It is, however, what can make you a successful business person if you do it right and get lucky.

This clip never gets old. Founder life is sometimes like this, often much less exciting.

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