I work in an online marketing company. It is a small startup company and it feels like a family. The partners, CEO, and managers are great. I came up with a business idea that will be in a market that is totally different than the company. I want to pursue this on the side and it won't interfere with my work at the company.
Would it be a bad idea if I pitch it to the CEO to try to get some funding for my side business? I just don't want people to think that I don't like working there or am thinking about leaving. It seems like a risky move but the CEO is so well connected that it is tempting to pitch it to him.
First let me say that, as always, my advice here is based just on the facts you've given me. You may know things about your relationships and office culture that should direct you differently. That said, I think it's a bad idea, for a couple of reasons:
1. You'll be putting your CEO in a really awkward position. This isn't asking someone to buy your kid's cookies for a school fundraiser; it's asking for substantial sums of money. I would be very uncomfortable with an employee asking me that. And I think it's highly unlikely that he'd say yes, since doing so would impact his primary relationship with you (making him your investor, not just your boss), and possibly even pose a conflict of interest. He needs to be able to manage you as your boss, not as someone with a financial stake in an unrelated side project of yours.
Of course he can just say no, but then you're going to be the guy who had the poor judgment to think this was a good idea.
2. The start-ups I've known have required so much focus and commitment from their employees that it's hard for me to think you could start your own side business without cutting into what's expected, or without at least raising that concern. They're going to assume that at a minimum, your focus will be split.
They're going to think this anyway, even without you hitting up the CEO -- but by pitching him for funding, you'll confirm that you are indeed going to be bringing it in the office.
I'm curious what others think though. Anyone ever done this successfully or think it's a good idea?