Real Estate and Death (hold the taxes)

Readers and Friends –

Welcome to my second newsletter and thank you for reading. You can read all (one) of my previous newsletters at archive at my blog –

I hope you’ll treat this letter as one side of our “asynchronous conversation”… I really want to hear from you.

If you like this, please share, if not – let me know – this is a work in progress… and if it isn’t a good fit, definitely unsubscribe and I wish you all my best.

As of today, there are 3 of you – thank you all again.

I’m on target with one article and one newsletter a week – thank you for helping keep me on track!

Cryptocurrency continues…

The article on cryptocurrency keeps growing. There are now 4 business models and I’ve identified 3 more that I want to discuss. I hope to finish it up in the next two weeks.

… and rethinking my “blog writing”

My old blog, PlayNoEvil, was written in classic “blog” style. A nearly daily diary. Always moving forward.

This time, I’m keeping working to keep my content “living”.. get it out there, but continue to make it better and more useful.

Tactically, this is better for SEO… but, really, it is about “cultivating my content” to better serve my readers.

The Real Estate Investing Business… mostly slow, intermittently terrifying

As a resident of the SF Bay Area, real estate is basically out of reach. Quite ordinary 3 bedroom, 2 bathroom houses in my neighborhood are approaching $2 Million… madness.

In the Fall of 2015 some friends and I started discussing investing in real estate. By early, 2016, they’d all moved on, but I was seriously intrigued:

  • Investment real estate is totally unlike home ownership. It is a business where everything is deductible, maintenance, utilities, interest, everything… and if it isn’t deductible, you can depreciate it …(and we’ll come back to depreciation).
  • Real estate is like stock picking – you can find hidden, undervalued gems if you look hard.
  • Real estate is like investing in options (which I would never do). because you can buy with lots of leverage… BUT, someone ELSE is paying for that leverage (your customers/tenants), and you typically have decades to pay-off or cash out your leverage.
  • Real estate is like a typical business in that your capital assets are depreciatable, BUT for real estate, that means the building itself (not the land), so you are basically being reimbursed for your total purchase (including leverage) over 27.5 years for residential real estate.
  • The US tax code loves real estate investing.

So, I started with a single family home… in Florence, South Carolina.

The start was rough.

Expensive lessons were learned.

My wife and I now own 4 properties (13 “doors” or residential units), mostly in Columbia, South Carolina.

It is hard to do real estate full-time. Especially remotely if you aren’t managing or maintaining properties directly.

It also takes time to identify properties, purchase them, rent them, and then build up or find the capital to do it again.

You can go faster with “hard money” or private loans, but it is still a part-time business.

We’re just wrapping up rehabbing an 8plex that we bough a year and a half ago… it looks like it will be a solid success, but I probably won’t buy something that big again for a while. It was basically a slum when we bought it. We’ve turned it around and it is part of reviving its neighborhood.

We’re providing a good home at a fair price for our customers.

One of the interesting issues/opportunities I’ve identified is that there are lots of properties that have been owned for a long time by the previous generation of real estate investors. Baby boomers who’ve done well, but are getting close to (or already at) retirement.

… and they don’t seem to have a good plan for what to do with their properties.

So, I put together an article working through “real estate exit strategies“.

Someone should probably write a similar paper for business exit strategies… (not the same as the excellent book “Built to Sell“)

… it is a bit of a stylistic experiment – comments welcome!

I probably won’t be writing much about real estate. As I said, it is mostly slow.

Systems Collection

I added two entries to my systems collection this week. I’m hoping to add some more – Derrick Reimer went through an interesting list of start up criteria on the Indie Hackers podcast that I haven’t captured yet – and maybe a fourth “Theory of Constraints” from the Startup to Last podcast and a fifth “Half time on marketing / half time on product” that I’ve heard a couple of times recently.

Disability Activism

I’m two weeks into the “break up” of my disability activist organization. Still feels right. During the Derrick Riemer interview, he talked about the failure of his “Level” (?) project and how he took some time off “in a cabin” to reevaluate and reset.

With two small kids, going to a cabin would be far from restful and relaxing… but I’m taking the rest of June to continue to pack for our move and reflect on how to proceed.

I’m converging towards a sustainable plan… but I want to “breathe” into it before leaping…. and, realistically, June is a mess.


Packing is going pretty well. More than 50 boxes of books packed and well into my rather absurd 800+ game collection – less than a month to go.


My game design / business strategy is also coalessing. I want both it and my disability activism to be very long-term sustainable and satisfying. I’m riffing on both content and Rob Walling’s Stairstep Approach to bootstrapping a business (another system to add to the collection…).

Battleship Poker is looking like the right game design to lead with.

More to come.

Learning Clojure (OK, starting…)

I am a mostly self-taught programmer, though I had a lot of software development training, I wasn’t there as a developer, i was there as a security guy who had to work with developers. My main programming experience was with ActionScript (the programming language very similar to Javascript for the Flash plugin…yep, I’m old) and Java for our game security middleware (around 25 thousand lines of code with a version ported to C on the Sony PS2, and C++ on the PC so we had cross-platform, cross language compatibility… pretty slick… just no customers!).

As our game security business was winding down, I was looking at rearchitecting our software (what was I thinking?) and, interestingly, the way I was thinking was very similar to functional programming…

So, earlier this year, I started looking into what I should be programming in. I’ve done some PHP too, Javascript seemed tempting, (Ruby?), but I didn’t jump in.

Then, for some reason (by way of Elm, but I don’t remember what got me there), I stumbled into Clojure.

Clojure is a functional programming language written on top of Java. It is a Lisp dialect (… one of those languages that I’d never gotten around to learning but which had always intrigued me).

It has a “twin” implementation, ClojureScript, that is written on top of Javascript.

So, same language for both the client and server AND access to all of the tools and libraries of two of the most popular languages…

… and some very powerful programming features.

… and great productivity and stability.

So, it seemed like a good time to maybe “skip forward” a generation and learn something new.

(though not too much just yet … see “packing” above)

No-code, low-code, … just code.

Actual programming language productivity is getting so good and the availability of amazingly powerful libraries … the challenge is more to figure out how to find the tools to build what you want.. avoiding vendor and platform lock-in… this is what we really should be teaching programmers

… not No-code, but how to code powerfully while writing as few lines as possible.

Back to packing

All my best.


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