It can become a full-time job analyzing and scrutinizing investment opportunities. There are many asset classes, different levels of risk tolerances, and various estimations on rates of returns. Analysis paralysis is very real and very common, especially among those who are deeply conservative in our risk tolerances. I truly understand because I am a conservative investor as well.

Over the past 20-25 years of my active investing journey, excluding mutual funds, 401k, and other similar passive endeavors, I have personally worked very hard to pare down the complexity to avoid too much stress in my life. Currently, my two primary active investing activities are real estate and private equity angel.

As a small real estate investor starting out 25 years ago, I focused on buy-and-hold rental properties that cash flow very well. For example, I would only get involved with properties that I was able to purchase and remodel for a grand total of $100k. This property would rent for $1500/month with room for an annual 5%-8% increase. The ability to make cash offers and then refinance after a year or two helped tremendously maintain decent equity while keeping the debt service ratio low and manageable.

Real estate is a wide spectrum of niches. Although I started in buy-and-hold rentals, I didn’t stay in that niche. I monitored the market conditions very closely, and when “flipping” became more profitable, I sold my portfolio of rental properties. I would continue to do “flipping” until the acquisition and remodeling costs became too high for any sufficient margins. Then I switched to private lending towards the latter part of my real estate investing journey. Private lending is far less active, but I still perform very stringent due diligence on the property potentials and the person(s) borrowing from me due to my conservative nature. I would prefer not to foreclose on someone, but it has happened a few times.

Angel investing in tech startups was a niche that I got involved in just 5 years ago. I belong to 3 local angel investor groups, and the sense of community and camaraderie is heart-warming, to say the least. Each group has monthly pitches and social gatherings. We perform due diligence together, and we debate the strengths/weaknesses. It is fun to be a part of such groups. It is also smart to harness the collective wisdom because that often leads to strong financial returns.