Besides the name issue (leaky) and the giving-your-sensitive-data-to-a-small-startup issue, one other thing that I question is how sticky is this startup? That is, how often will you visit it? Once a year, tops.
If you find an insurance that you are happy with, you'll likely stick with it for a couple years at least, and there is no reason to visit this website during these years.
Given the above, I don't see how they can ever make a ton of money.
I suspect that the referral fees from the insurance companies are paid out as percentage of the premium for the life of the policy. If so, that would add up fast.
Assuming people pay ~$500/year, and assuming 200 million drivers, and leaky gets x% of the drivers and y% of each premium, then they get $10xy million per year
If x% is 1%, and y% is 1%, that leads to about $10 million per year. Not too bad, if they can get those sorts of numbers for x and y.
One question would be, how long will people use them for, once they find a good insurance company? I've stuck with one insurance company for the last 10 years. I suspect that x will start low, and then grow as the company becomes known, and then shrink as people stop using it.
If you find an insurance that you are happy with, you'll likely stick with it for a couple years at least, and there is no reason to visit this website during these years.
Given the above, I don't see how they can ever make a ton of money.