I'll save the full story for another time, but incredibly two things happened at a Halloween Party in Bombay:<p><i>1)</i> The brother of the founder of my web app's chief competitor was there
<i>2)</i> We made that connection<p>He suggested we meet. My question: Should I meet face to face with the CEO of my chief competitor? If so, how do I approach it?<p><i>Pros:</i> Could get his perspective on industry, have an interesting conversation, make a contact that could potentially help me.<p><i>Cons:</i> May inspire preemptive competitive response. I'm not sure its good to alert someone before you throw a brick at them.<p>Here are some facts that may or may not be relevant:<p>1) I have a prototype ready, have raised some seed capital and will be raising a bit more shortly. I don't expect to launch the product until at least February. The competitor site is well established with 20M uniques per month.<p>2) They address a different niche in the market, though we overlap some (think Macy's versus Patagonia). They've positioned themselves for a different portion of the market, and appropriately addressing my niche would cannibalize their bread and butter. But I'd hate to underestimate them.
Maybe it's me, but I don't see the downside to meeting him. It's not a good idea to alert someone before you throw a brick at them, but it doesn't sound to me like you are throwing a brick at them. You're addressing a different niche, and without knowing anything about what industry you're in, I'd bet dollars to doughnuts that the number of customers you are going to poach from each other is miniscule compared to the number of potential customers that are not buying from either of you.<p>In my last start-up, I had a good relationship with the CEO of my major competitor, even though I disrupted what was a very comfortable situation from him, and took a lot of business away from him-- and we were battling for the same, very small niche. I had a lot of respect for him, and entertained take-over proposals on several occasions.<p>So, my two cents: go for it. Be respectful and humble, share only as much as you are comfortable sharing, but be honest in what you do say.