Cute and fun. I'd try the app if it had this page.
As a working designer, there's a few things I love about this guy's approach:
* use real language, not lorem ipsum. Text is half of the design.
* branding is just as much about giving personality as it is choosing a visual treatment, like "playfully nerdy with Jedi references" here or "sleek VIP club" like with Exec. The people that ripped on last week's mocks don't get it - design is a conversation-starter. Don't like the exclusivity of the previous mocks? Cool, then let's hone in on what you do want and guess what, some stuff from previous iterations might carry over.
* go straight to high fidelity, none of this nonsense of wireframes and personas and other deliverables that many PMs and designers are obsessed with. If you want low fidelity to quickly brainstorm, it's what paper, whiteboards and Starbucks napkins were invented for.
* speaking of high fidelity, don't be afraid to use real textures and take a stab at the logo too while you're at it. Designers that swear they love Swiss minimalist grids as their style usually turn out to be like the bad contestants on Top Chef that get weeded out early on because their style is "rustic". Riiiight, it's not because you don't have the knife skills to do Asian cuisine, sauce skills to do French, or baking skills to do desserts.
* and the thing I like the most is that he took the initiative to just put something out there. Even when you're working in-house, sometimes you have to grab ahold of the conversation and ship something real, something people can sink their teeth into instead of spinning out into orbit with conversation. It's also very common not to know what you do or don't like until you see some alternatives. Hey, it's called being human.
And trust me, you can cool it with the disrespect angle. None of the targets of these redesigns feel disrespected, since everyone's dying for design help and even just a few spare cycles from experienced pixel pushers. I tried an experiment of holding office hours for just one YC batch (S11, because I'm friends with Jason from Ridejoy) and my last two Saturdays have been booked completely solid. And Justin reached out to me a few weeks back about helping Exec's visual design and we haven't been able to get together, probably because of post-Demo Day craziness, so how happy do you think he was to see the free mocks from last week? Justin didn't ask for any shady spec work, some guy was just fired up to help out on his own dime. Right on.
(thankfully there's less naysayers on this thread so far compared to last week's one about Exec, just a boatload of feedback on possible alternatives. Yay HN, reminds me of the days of old :)
Like I said, love it. This is the quality of work I get paid to deliver and if I had to break into design or the SF startup scene all over again, I hope I'd be smart enough to do a series like this. It worked for Dustin Curtis with American Airlines, Metalab with Zappos and even 37signals did it way back in the day when they were a design shop. They did some unsolicited redesigns of FedEx and other brands that led to a lot of client work for them. I read Jason Fried saying somewhere that it was a smart move for them and didn't get why more designers don't do it.
[edit: added the paragraph about unsolicited designs not being disrespectful]