Internet Marketer Question ... Being Too Skeptical vs. Being Too Gullible

We're constantly having "opportunities" pitched to us -- not from direct competitors, but from others working on the same issues. Our venture is a social enterprise, so in addition to trying to make money, we work with non-profits, individuals and other companies working to advance our social mission. Basically, we approach all of these in the same way as I described above. Are they going to advance our vision? Do they fit into our plan or can we adjust our plan in a way that will enable us to better advance our vision?

Here are some examples:

1. We get tons and tons of share-for-share requests on Facebook. 99% of these we ignore, because frankly having a 100-member Facebook page share us doesn't buy us anything -- we have over 700,000 followers of our own that we reach six times a day.
2. We get tons and tons of sales pitches asking for 15 minutes of our time. Again, we ignore 98% these because we don't need what they're selling. Today, though I did actually set up a meeting with a website that wants to talk about their affiliate program. But it's a site we already knew and were thinking about, so it fits directly into our plans.
3. We also get interview requests from the media not infrequently. Frankly, media doesn't do much for the bottom line, but it does help advance our social mission. So we evaluate those on a one-by-one basis. For smaller publications, we'll usually consent to do phone interviews, but not written interviews (where they send a ton of questions and expect detailed responses. These can take forever. But for larger publications, we'll do them.
4. We once had a major advertising firm ask if we might be willing to consult on a campaign they were running for a major consumer brand. Consulting is definitely out of scope for us, but we talked to them and told them we'd be willing to help, but only because they only wanted us for an hour. If they had wanted us for weeks or days, we probably would have said no.
5. We were also invited by the US State Department to go to India to meet with people and to talk about the types of issues our business addresses. But other than credibility (if anyone even learns we were to go), I don't think we'd get any real business value from a trip like that. And yet... we still said yes. Screw the plan! It's a free trip to India!

Yes, Frank all successful business operators should perform their due diligence. But only after they overcome a certain amount of skepticism. If you're over skeptical you don't even bother with due diligence. At least I don't. Could I have missed some opportunities? Now we're back to the original question.

To be honest, I'm quite skeptical myself. Maybe it's because I'm a copywriter so I'm used to hearing exciting descriptions of things, maybe it's just because I've seen so many ideas fall apart completely.

One of my rules is to never get involved in something I don't understand. If there's a business, website, or even individual who I can help, I will always make sure I understand the market or concept before agreeing to anything.

The reason for this is that you need to be able to analyze the benefits and risks of any opportunity. If you know very little about the market, individual, or business then it can be almost impossible to do a real risk assessment. This is why I always start with a consultation where I attempt to understand the project as thoroughly as possible.

Then I will do a value judgement. First, I start with the person in charge. Do they know what they're doing? Have they done this before? Have they succeeded at similar things before? Are their priorities in the right place?

Then I assess the business. Does it have what it needs in terms of infrastructure and employees? Is it differentiated enough or positioned properly for the target market? Is it filling a need or is it just one of many businesses in a saturated market?

With that information in hand, I can assess what I might be able to offer. Can I actually help? Do I have fresh ideas? Do I have any established connections that will help? Do they actually need my services or is the problem located elsewhere?

This is usually how I analyze any potential opportunity like the one you've described. Risk is an important factor in both life and business. Risk is where you make the most money but it is also where you lose the most money.

The richest guy I've ever known said: You need to find that perfect balance between enough stability and just the right amount of risk to make the venture profitable.

The more you know, the easier it is to find that balance.

I agree Steve, either choice can hurt you. But my question is how do you personally get and/or maintain that balance ... consistently. That's what I'm looking for.