Adventures in Individual Investing

My journey - investing one Twitter recommendation at a time.

Welcome! The first thing you should know is I have very little idea what I am doing. The second thing you should know is I spend a large amount of time reading things from people who do seem to know what they are doing. Hopefully, by reading this you get an idea of what “not” to do and what things might work for the more amateur investor.

What follows is my adventure in investing. Generally, I subscribe to the "boglehead" philosophy that index investing is the surest way to guarantee your future financial success. The line of thinking that, over the long term, it is difficult to beat the markets rings true to me - and there are many studies that lay that out. That said, my father always said “everyone needs a hobby” - and mine so happens to be investing. I also do believe there is an opportunity for an individual investor to get an edge. Specifically, in looking for opportunities with asymmetrical risk / reward that smarter people might see - but just not be able to fully take advantage of because they are just too big. If you are moving hundreds of millions to billions of dollars around, though some microcap might intrigue you - the juice won't be worth the squeeze. For me, lowly individual investor, these sort of opportunities are what I aim to capitalize on.

I am fortunate to have enough in savings that I can keep plowing money into the market in index funds while also having a relatively sizable chunk to play with. As always, due your own due diligence - nothing I write here should be construed as investing advice.

Some history:

I first started playing with after-tax money in early- to mid-2018. Since that point I have put away $190,500 across a few different accounts.

When I had a large chunk to invest I became enamored with small-cap value. Specifically, the Ultimate Buy & Hold (UB&H) portfolios discussed by Paul Merriman. That uhhhh, has not worked out so well. The biggest chunk I invested was in June 2018 and, as you see below, that wasn’t the best idea:

This account is at M1 Finance - I sold out of about half of my positions in the UB&H portfolio earlier this year to plow some money into tankers. This has not panned out as well as I hoped initially, but a bag-holder I will be.

I’ve long held a robinhood account that is dear to my heart even though it’s fairly infuriating when it…stops working. But the colors are pretty. Right now that’s mostly for crypto and also has some tankers. Trying to get out of the tankers via covered calls, but most haven’t hit yet.

Final account is a TD Ameritrade account I funded fairly specifically to buy $CYDY on the advice of a random fantasy football message board. I was in at $0.50 and managed to make a pretty decent chunk of change on it. I’m still holding a mere 2,500 shares because it’s either a scam or management is just awful at…business, but we shall see. Free rolling at this point. I’ve had some real nice winners in this account - $AYRSF (thanks, @AaronValue), $ORRCF (thanks, @ClassicValueInv), and hopefully $BMYRT (@SheepOfWallStreet) joins the list.

Current Holdings:

As of writing my initial investment is currently worth ~$218K. XIRR based return is 9.66%. Had I just put everything in VTI the portfolio would be worth ~224K. So, currently trailing by about a percent or two.

As shown below, gigantic underperformance in UB&H & Tankers - large outperformance in the more actively traded TD account. Large part of me wants to roll the M1 into the TD account and start playing a more active role - but feels too much like capitulating so will likely just let it roll and hope for the best. Even @Joakim sees tankers doing well in the long term.

Current holdings are shown below. Will go in more depth for the bigger ones in subsequent posts.

In the meantime, tell your friends!