I think a single brand is a better option in this case because it greatly reduces scope, and seeing as it's a one man business scope is the biggest enemy there is. But also because I don't see it as a black and white decision about whether to appeal to geeks or enterprises.

I think patio11 went too far towards the "only appealing to non-geeks" end of the spectrum, partly because he just wanted to show how big of a spectrum there is. It's absolutely possible to have a optimized pricing system, and a well-designed (not talking just visuals) homepage without being anti-geek. For evidence of that just look at Stripe or GitHub. It actually seems like an incredibly rewarding task if cperciva finds the right geek-oriented designer.