Like wearing shades at a resort's pool with hooters waitresses they paid to hang out with and a lambo rented from Turo. 

I talked to waiters and waitresses, store clerks, park rangers, and small business owners. 

The millionaire man getting involved with the beautiful waitress is much more common than the millionaire woman getting involved with the handsome Burger King cashier.Not specific to this anonymous successful investor and the original poster, but in general, in these types of situations, if they become romantic, without all the details, who's to say who is taking advantage or who?

Hell, waiters and waitress's at average places clear $200+ per shift in tips alone. 

Instead of a conference room in a hotel type of setting, I would prefer more of a darker lounge type of setting with waitresses and drinks available (Even though personally I do not drink).

In my youth, I had a very short career as a waitress.

My 17-year-old daughter is still in high school, but she saved up $20,000 in 14 months as a waitress in a town of 10,000.

When you go out to eat and have a nice meal and great service, do you stiff your waiter/waitress too? 

Buying them lunch presents you the opportunity to learn from their past without making the same mistakes yourself.As the hour begins to draw to a close, I make sure the waitress knows the order is all on one check and that it comes to me.I use this strategy to turn lunch into a “lunchinar” as often as possible.

Most people seem to avoid the conversation about all the Real Estate risk takers that played the biggest part in the housing crisis.A few years before the bubble burst I was encountering real estate investors, house flippers, and buy-and-hold participants everywhere I went, my waitress at The Cheesecake Factory, the two McDonalds employees talking deals on their lunch break, the clerk at the grocery store, everyone everywhere appeared to be a real estate investor in one form or another getting a piece of the housing boom.The underlining problem I noticed was during the rush to get into the RE industry most of the people capitalizing in the industry never learned the basics of RE investing and were simply doing what their friends, neighbors, coworkers, or online postings told them to do to get a piece of the pie.