Seth Godin recently wrote about the two kinds of "hustle" in startups. Here's my take on the role of the dealmakers.
There's the hustle of always asking, of putting yourself out there, of looking for discounts, shortcuts and a faster way. This is the hustle of it it doesn't hurt to ask, of what you don't know won't hurt you, of the ends justifying the means. This hustler propositions, pitches and works at all times to close a sale, right now.
This kind of hustler always wants more for less. This kind of hustler will cut corners if it helps in getting picked.
Then there's the hustle that's actually quite difficult and effective. This is the hustle of being more generous than you need to be, of speaking truthfully even if it delays the ultimate goal in the short run, and most of all, the hustle of being prepared and of doing the work.
It's a shame that one approach is more common (though appropriately disrespected), while the other sits largely unused.
In business, especially startups, I've seen what I'll call the "entitled" hustler in almost every organization. They go business to business, opportunity to opportunity constantly trying to sell and close.
That sounds great, but FEELS embarassing. Why? Because, in my opinion, it feels like constantly asking for handouts simply because they're a startup (as if that differs somehow magically from any other new company). That sense of entitlement is a putoff because it doesn't have any long term value.
The second type, those who are looking ahead, making plans, and being honest about the stakes, expectations, and deliverables are working to forge lasting relationships. These are the hustlers that not only willing to talk the talk, but walk it and dig into the trenches. These are the folks who I feel I can trust when we're trying to lay everything on the line--and who respect MY business as much as I respect theirs.
As an aside, I still think hustler is such a strange word for the role assigned to the business side of a startup. I get that they're 'hustling', but the negative connotation constantly makes me laugh when I hear it. What's a good rule then? Don't embody the NEGATIVE connotation of hustling. ;)