1. The batting cage idea is very risky. I’ve seen many of them close over the years and it is not anything close to passive income if you want to keep the business going. You have to continually promote it and target youth leagues, coaches, schools etc to catch all of the new players who grow up and want to play. I’ve played at probably 8 batting cages over the years and 7 of them closed.
What I’m doing: I use this site to write out goals like 1) Generating $200,000 a year working 4 hours a day or less, 2) Trying to make winning investments, and 3) Keeping track of my passive income streams with free financial tools. My site and the community helps keep me accountable for progress. It’s important I do what I say, otherwise, what the hell is the point? You should consider starting a site or at least a private journal. Write out your specific goals, tell several close friends and stick to the plan.
Pardon for being a bit of a newbie to true investing outside of a 401k. What about those of us who have 1) Just been laid off, and unable to find work due to lack of a degree (apparently 17 years in the industry with 5 certifications is just simply not enough – which is okay. It gave me the kick in the arse to get back to school finally) 2)Have three children to support (age 11 and under), and 3) Oh yeah – cannot find work. What do you recommend when the only source of positive revenue has ceased to come in and you now have less time than ever – due to responsibilities (i.e. doing well in university = academic scholarships means investment in time, plus spending 20 min breaks with kiddos) – to create positive sources of income ? I truly am wondering from an investor’s point of view how you would handle the pivot point of life if ever you had been faced with it. I realize this may be only imaginary, but at this point, I welcome your “what ifs” scenario on this one. You’ve truly done amazing work and I thank you for being so transparent.
For those of you who don’t want to come up with a $220,000 downpayment and a $900,000 mortgage to buy the median home in SF or NYC, who don’t want to deal with tenants or remodeling, and who wants to not do any work after the investment is made, check out Fundrise. They are my favorite real estate crowdsourcing company founded in 2012 and based in Washington DC. They are pioneers in the eREIT product offering and they’re raising an Opportunity Fund to take advantage of new tax favorable laws.
I want to develop a passive income stream in the next 4 years, nothing grand, maybe an extra 500-1000 dollars a month, but I’m not sure how to go about it so I was wondering if you had any tips. I’m so-so as a writer, and am currently finishing up my second book (just write as a hobby), and in the past made about 30-50 dollars an hour as a free lance writer but that was a couple of years back, it was only for about 10-20 hours a month, and the gig just dried up. I just got particularly lucky with that. I’ve tried online poker as a means in the past, and which I learned A) was not passive income but hard work and B) I have an addictive personality which resulted in me losing the 4g I earned in 6 weeks over the span of 72 hours so that’s out of the picture. I also partook in some illegal selling of things when I was younger, but being a little older and wiser the risk-reward ratio for possibly ending up in Jail just doesn’t match up. I tried making three businesses (dog walking, house cleaning, and personal assistant) and while those all were succesful to varying degrees and earned me about 15-25 dollars an hour, they weren’t mobile and quiet honestly I don’t have the time to be a full time dog walker or run a house cleaning operation seeing as I’ll be in school, work, and athletics.
After these tenants move out, I'm thinking of just keeping the rental empty with furniture. It sounds stupid to give up $4,200 a month, but I really hate dealing with the homeowner association, move-in/move-out rules, and maintenance issues. Given that the condo doesn't have a mortgage and I have to pay taxes on some of the rental income, I'm not giving up that much. The condo can be a place for my sister, parents, or in-laws to crash when they want to stay in SF for longer than a week or two.
Capital growth in your portfolio can offset the eroding effect of inflation.  But any capital gains that exceed the overall inflationary effect can be drawn off to augment your portfolio income.  Of course, you must first generate those gains by making thoughtful investment selections.  While allowing strongly growing assets to keep doing that, it is prudent not to allow them to become a dangerously large part of your portfolio lest they go off the boil.  So if you selectively trim profitable positions along the way, you can boost your income.
After these tenants move out, I'm thinking of just keeping the rental empty with furniture. It sounds stupid to give up $4,200 a month, but I really hate dealing with the homeowner association, move-in/move-out rules, and maintenance issues. Given that the condo doesn't have a mortgage and I have to pay taxes on some of the rental income, I'm not giving up that much. The condo can be a place for my sister, parents, or in-laws to crash when they want to stay in SF for longer than a week or two.

An obvious example is over exposure to bank stocks, which have been excellent investments for over a century.  Though a foundation of most portfolios, bank stocks do involve more risk at certain stages of the economic cycle than many realise.  Being less exposed to bank shares in the last few months could have preserved some capital.  So, a more diversified approach can help mitigate some of these risks.
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