Shopping for commercial auto insurance (very small business idea)

I’m looking for guidance on how to find a commercial auto insurer to cover my manual transmission car as I rent it out to students (for money). This is assuming my regular insurance won’t cover me.

Justification:

In the last few months I’ve started teaching manual driving lessons through two companies. It’s a “gig” business model, where the companies provide insurance, marketing, and booking, and I get a flat fee per lesson. Lessons start at $300 for a 3 hour time block and go up from there, but the expectation is that students book a single lesson, I teach them as much as I possibly can in that time period, and then that’s it – no repeat customers.

The problem, of course, is that 3 hours is a long time. Legs get tired, brains get tired. Learning to drive a stick takes about 30 minutes, I can stretch it to an hour, and then the rest of the time is just practice. Time that would be better spent doing distributed practice over the course of a couple weeks. Let the brain rest, let the reg rest, etc. IME it’s really hard to get proficient at driving a stick if you do it once in a while, but if you do it every day for 2 weeks you’re set.

I’m permitted by these companies’ terms to advertise myself, but only if I direct customers to them for booking. Since I’ve signed up with multiple companies, this isn’t really an option. But my idea is that I have a captive customer in the car for 3 hours, who at some point will realize that they’re not going to become fluent after 2-3 hours. I’d like to be able to give them a card with a website where they can book time to just rent my car (similar to Turo, but hourly). I figure at that point I’ve already vetted whether or not I feel comfortable taking them out without me. I can meet them in a public location, give them a quick refresher, and then they can go drive around for an hour. If they do this 2 or 3 times it’s really going to help reinforce the learning.

I’m not going to get rich doing this, but it’s fairly low impact for me – I have a spare car and can walk to the drop-off point.


So, I’ve never done anything like this and I’m not even sure where to start. Do I just cold-call independent insurance providers? How do I find a good one?

Yes, find an independent insurance agent. They will know what companies offer the kind of coverage you’re looking for and can take of everything for you. Cold call or fill out a form on their website. (Strong personal bias - find an independent one that has appointments with several carriers. Don’t start with a carrier themselves.)

But I think you’ll find you actually want personal auto, not commercial. You own the car personally, even if it’s being used commercially in this case. The insurance agent will figure that out for you, but I wouldn’t start off by specifying you want commercial auto. Just tell them what you’re doing.