We want the Level Up site (and the logo) to draw stylistic inspiration from old-school 8- or 16-bit video games. But it's consumer internet product aimed at adults, especially in their twenties and thirties. It should evoke video games from childhood and make those people smile nostalgically, but it shouldn't look childish itself.
The challenge here is to evoke that retro-video-game vibe and make the logo fun or a little whimsical, while also making it very clean and professional. This is a corporate logo for an internet startup -- we want a logo that will go on business cards, that investors can take seriously, something that can be featured on the cover of Fast Company magazine. It should also be readable even when shrunk down.
Here are examples of startups whose logos I like. Some of these are more serious, and some more playful, but they all look professional. Take a look:
I've attached below a Mario-inspired wallpaper that gives a rough sense of the the look I'll be going for in terms of the website background. (But, of course, without the undeniable, copyright-baiting Mario elements -- the blocks, the eyes on the hills.)