I run several online businesses now (all it takes to start one is a domain, hosting, and maybe incorporation). There are two notable ones. The first is meal plan membership site called $5 Meal Plan that I co-founded with Erin Chase of $5 Dinners. The second is the umbrella of blogs I run, including this one and Scotch Addict. They pay me ordinary income as well as qualified distributions since I'm a partner.
In January 2018, I missed my chance of raising the rent on my new incoming tenants because it didn't come to mind until very late in the interview process. I didn't write about my previous tenant's sudden decision to move out in December 2017 after 1.5 years, because they provided a relatively seamless transition by introducing their longtime friends to replace them. I didn't miss a month of rent and didn't have to do any marketing, so I felt I'd just keep the rent the same.
Within six months of selling, however, I had reinvested the proceeds from the home sale and brought total passive income for 2018 back up to an estimated $203,724. I'm not sure I would have sold the house without a clear plan for reinvesting the proceeds, since I'm bullish on the SF housing market long term. However, because I did have a plan, and the challenges of raising a newborn and dealing with rowdy tenants left me feeling a bit stretched, I decided to simplify and sell.
Two months into my work hiatus and I’m doing well. I’ve made a little bit more than I’ve spent and I’ve worked about four hours a day on average. Ultimately, I’ll know I’m ready to make the permanent jump to a 4 day work hour when my passive income plus side incomes equal my day job income. Until then, I’m going to go back to my day job and keep grinding it out.
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.
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