I just went through​ this. Started as LLC with co-founders. Once we started seeking money we up-scaled to C-Corp - give the lawyer a few bucks, wait a week, sign some stuff. Mostly painless.

Going to a C-Corp too early can be costly, moving up from a proven model LLC is easy, limits cost and risk

Why not use Clerky? It's about a grand all-in, and since YCombinator uses them for all their incorporations, it's what all your investors are likely to expect.

Because it generates a Delaware C-Corporation, and a DE C costs more annually to operate than an LLC. Among other things, most small business operators want pass-through taxes.

Do you have any opinion on a pass-through Delaware S-Corp vs LLC?

Hmm, I'm not sure that's accurate. What would you be converting to if your company was already a C-Corp?

A C-Corp with the structure your venture capital firms expect.

There may be more structure required but starting off from a C corp obviates the need to transfer control of assets (particularly intangible ones like copyrights to source code).

You're paying a substantial amount of money up front to hypothetically mitigate a hypothetical future expense that only occurs at the point where cash flow (at least on the order of "covering legal expenses") stops being an issue.

That doesn't sound like a good deal to me, but that's just, like, my opinion, man.

Quantify substantial.

Last time incorporated a Delaware C corp it cost me a couple of stamps and filing fees. I don't remember exactly but it definitely wasn't an obscene number. The annual upkeep, including franchise tax and registered agents, is around $600.

If you're not going to have a nexus in another state (i.e. No physical location or storefront) then that's peanuts for having a corporate vehicle in the the state for corporate vehicles.

If the cost difference of a couple hundred bucks is enough to break your bank, I'd suggest finding a 9-5 job rather than incorporating.

Can you elaborate?

Operational and structural details like this have always fascinated me.

Part of the premise of Gust Launch is that it's far simpler to start this way, as a Delaware C-Corp with expected structure, than it is to convert later. The conversions range from easy to extremely painful but they're almost all avoidable.