I invested in Gold as per Allens advice and when the big stock market crash occurred in 1987, I made a ton of money by being in other investments such as gold. Ditto for real estate that market plummeted inthe 80's. Following Allen's advice, I was able to pick up loads of real estate at bargain prices becuase most real estate investors back in those days saw real estate only as a tax benefit, not for gains. Their loss.
Amazing that you saved between 50% to 75% living in NYC…I think that is one thing holding me back…the cost of living here. I’d like to invest in real estate, but I can barely afford to buy a place to live. I don’t need a large income to be happy, but I probably do need an income to support living in NYC as we don’t plan on leaving. The only thing I’m doing at the moment is saving in my 401K, IRA and a I dabble in stocks and P2P lending.
I’m looking at accepting a professor job. It’ll be more than a 50% pay cut. But I’ll have the same life you describe – endless summers and an entire month every winter to ski. I’m thinking in the end, eventually, I might even end up wealthier in more ways than one. Happy people tend to be the most successful. I have no desire to diversify. Dividend stocks allude me. CDs seem like a good choice for older people, but I have time on my hands and real estate knowledge, so I’m sticking with what I know, despite the fact that most people will tell me it is foolish and I should diversify.
When you build a business, you're giving up active income (instead of working for pay, I'm volunteering at my own business) for future active and passive income. In the meanwhile, you'll need a way to pay for your expenses. It could be that you're building a business on the side, so you still have a day job, or you're living on those savings. Either way, you need a cushion.
As for me, I started focusing on passive income last year, but have owned rentals for 5 years. $25k now outside retirement accounts in mostly real estate. Looking to invest another $500k cash into real estate to get about $65k, and then 1031 under performers next year to hopefully boost that a bit higher. Heavy in real estate, but feels lower risk than the stock market to me if you have cashflowing properties. Real estate is inflation adjusted, and built in cashflow raise when the loan pays off.
Thanks for the info…I kind of figured it is really not that expensive to live if you are not an extravagant person. I could definitely figure out how to funnel expenses through a part time business…I think I keep thinking along the lines that I’m going to be paying the same tax rate after retirement, but reality is you could get pretty lean and mean if one focused on it. On a scale of 1-10 with 10 being utter panic mode, how worried are you about your “pile” lasting through a 50 year retirement now that you are a couple years into it?
A business thrives or fails depending on its marketing and system for generating leads. You need leads to make sales. No audience or exposure means you won’t get fresh faces checking out what your business does. Too many entrepreneurs spend all their time on the “busy work” and not enough on audience building. There are some great ways to build an audience and generate new leads:

Other scholars suggest trading from India to West Asia and Eastern Europe was active between the 14th and 18th centuries.[62][63][64] During this period, Indian traders settled in Surakhani, a suburb of greater Baku, Azerbaijan. These traders built a Hindu temple, which suggests commerce was active and prosperous for Indians by the 17th century.[65][66][67][68]

As the third-largest economy in the world in PPP terms, India has attracted foreign direct investment (FDI).[301] During the year 2011, FDI inflow into India stood at $36.5 billion, 51.1% higher than the 2010 figure of $24.15 billion. India has strengths in telecommunication, information technology and other significant areas such as auto components, chemicals, apparels, pharmaceuticals, and jewellery. Despite a surge in foreign investments, rigid FDI policies[302] were a significant hindrance. Over time, India has adopted a number of FDI reforms.[301] India has a large pool of skilled managerial and technical expertise. The size of the middle-class population stands at 300 million and represents a growing consumer market.[303]
Portfolio income can come from multiple sources – interest/bond coupons, stock dividends, financial strategies including derivatives and capital growth.  Each offers some cash flow and some also offer potential capital gain with some risk from liquidity and volatile prices.  In this low-yield environment, many investors rely too heavily on cash flows and to pursue this are venturing further into riskier areas than they’d normally consider.