- Actually getting started. It's much easier to talk about starting a company - everyone thinks it is so exciting and gives you a 100 suggestions and you feel you're floating on air and are high on enthusiasm. But actually start a company and suddenly there's a metric ton settling down on your shoulders - now you have to talk about reality, not dreams.
- Building a team. Yes, you have your best friend from college as your co-founder, but what if you say zig and he says zag? What if you can't find any good people with the right skill sets, for example, you can't find developers and you have to learn how to code (all over again)? What if there's nobody but you in your company?
- Having the right idea. You did talk to 100 people before you started, but they were friends of friends at that huge end-of-summer party you went to and though they all thought it was cool, it could be that they were in party mode. How can you be sure your idea is really good?
- Business plans. It's either a big mystery and you have no idea how to go about it, or, you know exactly what to do and hate the idea of having to re-word, re-calculate, re-format every time you show it to someone new.
- Getting money. What if you don't know any rich angels and your friends and family have slim wallets? Maybe you can bootstrap, but you'd have to figure out if there's a boot to strap (or a strap to boot) - and it has to work with your specific idea.
- Legal coverage. Lawyers cost money (see above), but could you get sued, cheated, conned out of money/stock/intellectual property if you're not sufficiently lawyered-up?
- Competition. The horizon is full of 800-lb gorrillas and pesky little startups (not yours) that want to do exactly what you plan to, and look like they'll get there faster and blow you out.
- Customers. Or users. What if they don't show up? Or worse, they don't show up only randomly and you can't show a chart-popping growth rate? Is it a bad idea or bad marketing?
- Time. As in the thing you can run out of, along with money.
- Expert advice. The blogs, the pundits, the classes, the social media groups, all making holding forth on why your startup will fail, and, to add insult to the injury, why your company is not even a startup because it doesn't fit some VC's startup profile or, to rub salt in it, why you will fail because you don't have the profile of a successful entrepreneur - wrong college, wrong age, wrong degree, wrong home town, whatever.
Happy Halloween!
