Should I take a chance and drive for O/O?

Looking for some advice on a situation I'm having trouble finding relevant discussion about: should I give driving for an O/O a try?

A formerly retired veteran, independently wealthy Ops Mgr w/15+ years experience in logistics I went to truck driving school with went O/O after turning in his keys a few months back. He got his own authority, runs 100% independent (brokers and boards only, no lease contract to anyone), has no debt aside from the truck he drives currently and he's planning to buy 2 more trucks. No more, no less. He wants to run a 3 driver operation that he can manage from his $100,000 boat, while driving a few days a week himself when he feels like it.

Since he started running, he's been pulling in $1k/day, net. He obviously knows what he's doing, he's been doing this stuff for years, without the driving part.

Now that he's gotten his feet wet and figured out how to work the boards and brokers and totaled out his operating costs, he's getting ready to buy 2 more trucks, irrespective of my decision (he'll find someone to fill the seats).

From our conversations, the way it would work is I'll drive one of his other trucks, under his authority, using his brokers (that he'll teach me how to use and dispatch my own freight) and I keep the net profits, minus some portion that I'm sure he'll keep to roll back into the business.

I don't care about benefits and I'm used to 1099 work and the hassle that comes with it. We haven't talked hard numbers yet, but I've still got some time to work that out before committing. I'm still employed (by a company I despise and can't keep me busy). My training contract is up in a few more weeks, have all my endorsements and credentials along with a clean CSA, MVR, and DAC.

My question is, is it worth giving it a shot? If it was some rando operation on Craigslist, I wouldn't even entertain it, but I've known this guy for a year now and consider him a friend (as I am with all my former classmates).

By my logic, the only real risk on my end is having to find somewhere else to go if things don't work out, which won't be an issue other than the hassle of it. It seems all the risk is on his end, to which I've already addressed: he knows I'm only in this for 1-2 more years while I finish my pilot training and I'm out. If the loads dry up or something else happens, he isn't concerned with me leaving.

The potential upside here, in my view, is huge. Run my own schedule, with his truck, hauling the loads I pick from his brokers. I don't see much of a downside (yet, but then again, we haven't hashed out official contract details yet).

Of course I'm not committing to anything officially until it's in writing, but what say you all about the opportunity?

Thanks in advance for any advice offered.

 

Well, the money is, and that's why I'm considering it, but no, I don't particularly care about the benefits. 2500-3500/wk (minus taxes of course) with minimal risk is what makes the offer so enticing.

 

Well, I trust a friend more than a mega like Schneider. They're a hard pass for me.

 

Counting fuel it's 1400-1600. Just got off the phone with him a couple hours ago. Ran 8 days, grossed 9600, spent roughly 1400 in fuel. And they were mostly broker loads. Rarely does he run straight off a public board, but it does happen occasionally.