Wow, that is pretty impressive. I wonder how they were able to hold onto those places for so long without the building owners trying to take them away and turn them into multiple units. They must have ironclad purchase agreements. My friend is kind of the same way with starting his own business. He waited so long and how he will be the first to tell you that he should have started sooner. The things he was worried about (namely health insurance) ended up not being as big of a deal as he thought it would be.
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I'm not sure how these people have managed to stay so long. I think some of them were just grandfathered in because of rent control policies and such. Health insurance was one of the main reasons I waiting so long. Before the Affordable Care Act was passed the only option was paying for private insurance and it was astronomically expensive. Now I don't pay much more than I did when I had my day job and it's actually way better coverage.
Good for them, I just think it's amazing knowing how much demand there is for real estate in NYC and what lengths people will go to when they see potential dollar signs. My buddy ended up getting remarried and his new wife had insurance. That was the big deal for him. Then he found out how successful he could be and it ended up not being that big of a deal. He has his own employees now and he makes sure he provides them with a very good health insurance package.
Yeah, the market is crazy there. Some landlords have done some unbelievable things to get longterm renters out of rent controlled apartments. I'm happy to hear about your friend's success! I think it's more of a mental barrier for most people when it comes to entrepreneurship. That was the case for me, I thought I needed the safety net of having an employer.
That makes a lot of sense. I am glad you finally took the dive!