Any tips for reducing my risk from an equity cliff when joining a startup?

Don't accept an unreasonable paycheck. Options, cliff or not, are just icing on the cake. Don't expect them to have any value. Usually they don't, as you already found out.

Ask for the vesting to start immediately prorated on a monthly basis over the first year, with an initial up front grant for coming on board.

Its been said in previous comments but if you're getting underpaid, don't accept a clean cliff. Either they pay you market rate and you get a cliff, or you get paid under the market rate and you get some sort of equity vesting without cliff.

Yeah, accepting that deal was obviously a huge mistake in on my part in retrospect. I was fooled by "standard" documents and thought it wasn't negotiable. Will definitely discuss a more appropriate arrangement this time around. Thanks everyone!

I would attempt to negotiate for pro-rated vesting first and if that failed, a perk with actual cash-value for you prior to the vesting. E.g., 50% coverage on spousal health care, monthly transit card, paid meals after 7PM, something.

If the company rescinds their job offer when you attempt negotiation, you don't want to work there.

How did they get funding without a tech resource in the first place? Just on the biz plan and connections? If so, that's another reason to follow the advice above and insist on gradual vesting and a good paycheck.

Maybe you care telling us how the funding went down...

Plan, past startup and industry experience and the connections that comes with.