If you are not able to get a mortgage on the property, there are still a few options available though rates can be fairly high. You might try approaching the seller for owner financing where they sell the property to you on monthly installments. This might not be possible if there’s a mortgage on the property since many carry a “due on sale” clause. If you do go this route, make absolutely sure you get a notarized contract with all the details.
Anthony, nice setup! To your question about the rental mortgages, you haven’t said what interest rate you are paying. As a start, if you are paying more than the risk free rate (Treasury bills) which you probably are, then a true apples to apples comparison would be yes, pay off the mortgage. But, if you are comfortable taking more risk, you have other options to invest in which you *hope* will yield you more over the coming years. You also didn’t say whether the rentals generate net income and if so, how much? What is the implied rate of return on the equity you have invested in them? If you pay the mortgages off, you’ll have even more equity tied up, will the extra net income make that worthwhile? Maybe you should use the money to buy more rentals instead, if purchase opportunities still exist in your town. … this is less of an answer than a framework to analyze the decision, hope it is helpful.
I have been a open minded driven dreamer since i was 18. Mix that all in with a complete screw up and you got my identity pretty much grasped…. There have been many different jobs that I have held since graduating High School. A side from my dads asphalt company and one landscaping gig I’ve been in sales my whole professional life. I am 33 years old and I know about the Insurance, Banking, Industrial/Electrical Manufacturing distribution, Telecommunications and Finally “online distribution” AKA: EBAY.
I just can’t seem to get my head around creating my own online product. When you talk about it, you make it sound like its mostly just about putting in the time and plugging away at it. Problem is I can never seem to come up with any ideas for a site or product that seem remotely unique or compelling or that I have any special knowledge about. The stuff I do know about is pretty commodity type knowledge that can mostly be found on thousands of sites on the internet already. Any tips on discovering what your “unique angle” is? I mean, you have a pretty compelling and somewhat unique personal story of working on wall street and then walking away at a young age.
Now I’ve been using Swagbucks for a while and have found the money works out to just under $2 an hour so this isn’t something that’s going to make you rich. You’d have to work 2,500 hours to make $5,000 so that’s about three and a half months, non-stop. The thing with Swagbucks though is you can do it when you’re doing something else so I flip through surveys and other stuff while I’m cooking dinner or flipping channels.
Buy a small business: A local small business, like a car wash or a laundromat, is a great way to put money down on a money-making venture. Automate it so you don't have to be on the premises unless you're collecting money. Go into a local business with your eyes wide open - study the books, especially on income and expenses, and examine water and utility bills if your venture will be open 24 hours.
ie first you need to haul ass and do something crazy, eg write a quality 20,000 word ebook (insanely not passive hahahah), but then you get to sit back and enjoy seeing PayPal sale messages pop up on your iPhone each morning as sale after sale after sale is made…on an ongoing basis and without any additional work. That’s some seriously Pina Colada flavored passive goodness!
It’s a (mostly) short term, higher risk, higher reward place to invest cash that has a low correlation with the stock market, but is far more passive than buying and managing properties, has more opportunity for diversification than private placements (minimums of 5-10K, rather than 100K), and most of the equity offerings (and all of the debt offerings) provide monthly or quarterly incomes. Unlike a REIT, you can choose exactly which projects you wish to invest in.
​Udemy is an online platform that lets its user take video courses on a wide array of subjects. Instead of being a consumer on Udemy you can instead be a producer, create your own video course, and allow users to purchase it. This is a fantastic option if you are highly knowledgeable in a specific subject matter. This can also be a great way to turn traditional tutoring into a passive income stream!
Unfortunately, I can’t answer that conclusively one way or the other. It all depends on you, what you like to do, your work ethic, personality, etc. If you are a good writer perhaps you could write a book and make money that way. Or, you could start your own website and do affiliate marketing. Just because you are young it doesn’t mean you can’t make money doing at least a few of these ideas. I wish you luck in your money making efforts!
Venture Debt – I invested $120,000 in my business school friend’s venture debt fund. He started his own after spending 8 years at one of the largest venture debt funds as a Managing Partner. I’m very focused on income generating assets in this low interest rate environment. The true returns are yet to be seen, as the fund has a 5-7 year life before it returns all its capital.
Real Estate: I currently own one rental property in San Francisco which I bought in 2003 (2/2 condo), one vacation rental in Squaw Valley, Lake Tahoe (2/2 condo), and my primary residence. Real estate is my favorite asset class to build wealth because it is easy to understand, tangible, provides utility, and rides the way of inflation. I recommend individuals try and get neutral inflation by buying their primary residence as young as possible. The power of inflation is just too hard to counteract.

* I use Personal Capital to track all my finances in one place. It’s much easier to use their free software to follow 28 accounts on one platform than to log into various accounts to check my balances. They’ve also got great tools for x-raying your portfolio for excessive fees, recommending a more optimized asset allocation, and planning for retirement with their Retirement Planner.