Can an old tech guy learn new tricks?

Cross posted from Old Programmer

Hi. I’m DJ, an old programmer. I am 55 years old and live with my dog, Monkey. Here we are.

I live alone, but I never get lonely. Maybe it’s because I’m an INTJ?

This is my first post. This newsletter is an occasional journal, links to resources I like, discussion of macro trends in tech and advice for people looking to work as a software engineer. If any of that resonates with you please smash that subscribe button below

The Backstory

From 2017 to early 2023 I did commercial real estate investing. That is, I worked with investors to buy and manage properties through a process known as syndication. Previously I spent about 20 years in tech, almost exclusively in startups.

How did I go from tech to real estate? Like this.

In 2016, the startup where I was CTO failed. I was burned out and had started doubting my abilities. I especially worried that I no longer had the relentless drive it takes to build a company from scratch.

To distract myself, I started learning about real estate. I went to meetups, listened to podcasts, joined Bigger Pockets, and learned how properties are valued, bought and sold. I got especially interested in apartments because of scale — why buy one rental when you can buy 100? All the gurus touted how great passive income is, and they made it sound easy as pie.

(It isn’t.)

So rather than go all-in on another tech startup, I… went all-in on a real estate startup.

We bought a few properties (after making offers on hundreds), put on some really popular events and built a database of over a thousand investors. The future was bright. Until…

COVID

In March 2020 we were scheduled to close on a 250 unit apartment complex in Oklahoma City. It had been a painful due diligence process that took much longer than planned. We had six figures of earnest money in it, had re-negotiated the price twice (there had been two fires at the property while under contract), and worked really hard to line up the capital needed to close.

Less than two weeks before closing, two of our key partners got spooked by COVID and pulled out. This triggered a a domino effect with other investors and, long story short, the deal collapsed. We lost most of our earnest money.

(Less than a year later the property sold for $1 million above what we had it for. It proved our thesis: this was a great deal! We just failed to execute.)

From there it was one headache after the other. The pandemic hit one of our properties particularly hard because it is in a tourist town. Sadly, our property manager died suddenly from a brain aneurysm. This meant I had to go take over the property and learn property management on the fly. I ended up moving there full time for almost three years.

In the meantime, inflation reared its head and the Fed raised interest rates faster than it had since the late seventies.

This is a Bad Thing for real estate!

I had never worked in an industry that is sensitive to interest rates like real estate. In fact, the only people in real estate who have worked in that environment have been in it since the mid eighties. 95% of today’s investors are in uncharted territory.

It was a learning experience.

What I Learned

I could list all the things I learned in the industry about risk, debt, equity, property management, and so on, but what I really learned is the hard truth:

I’m just not a Real Estate Guy.

I don’t get excited about rehab projects, or combing through listings, or touring houses just for fun. I don’t get pumped up from learning about real estate markets, or pitching to investors, or implementing value-add strategies or running a rehab project. And I really don’t like negotiating.

In my heart of hearts, I’m a software guy who loves to explore the boundaries of technology by digging into the nitty gritty of code.

Usually with a setup like this

So in 2023 we decided to wind down the firm. We still own one property, but it’s mostly in maintenance mode while we wait for the market to reset itself.

A few months back I felt myself stagnating and decide to survey the tech scene to see if I still fit in. I signed up for an online data science course in Python and quickly discovered a few things:

  • Though the technologies continue to evolve, the fundamentals are still the same,

  • Writing code again is like putting on a comfortable pair of slippers,

  • It’s easier than ever to write quality code, and

Ralph Malph I still got it

Gen-Xers get this

On the other hand…

I’m kind of, well, you know, old. I know we in the US of A are supposed to be an open, diverse workforce that welcomes people from all walks of life… and I also know that there’s still a lot of bias in the system.

Tech is generally seen as a young person’s game (I almost wrote “young man’s game”), and I can’t help feeling a little insecure about it. It might all be in my head… but maybe it’s not?

On the other other hand

I love writing code! It invigorates me. I knew I had to get back into it when I watched this video about lambdas in functional programming. To most people, this kind of thing is as stimulating as cleaning out the dryer lint catcher, but to me it’s manna from Heaven. I discovered it while reading The Imposter’s Handbook, which I will write more about in a future post.

What Next?

Wow, you made it to the end! I’m flattered. I will be writing more about what it’s like to be an Old Programmer. Please subscribe, and let me know what you think!

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Pivoting to Substack

It’s been a loooooong time since I posted regularly. Recently I got the itch to start writing again, but this time I’m doing it on Substack. My writing primarily focused on what it’s like to be a fifty-something programmer in an industry that skews very young. You can find it at oldprogrammer.substack.com

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Semi-Random Walks # 43: Artist and writer David Sandum

ill-run-til-sun-goes-downDavid Sandum travelled all the way from Norway just to talk to you. He’s written a terrific memoir called I’ll Run Till the Sun Goes Down, and it just so happens that his publisher, Sandra Jonas Publishing, is based in my adopted hometown of Boulder.

Listen in as he tells of the monumental struggles he went through, creating great art and even greater community along the way. Seriously, the dude has a rabid following on social media. I was turned on to him by a high school buddy (thanks Rob).

Follow him on Facebook and on Twitter @DavidSandum

 

 

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Semi-Random Walks #40 : Singer/songwriter/musician Latifah Phillips

latifahphillipsI really enjoyed this interview. Latifah Phillips is a prolific musician who writes, performs, produces, tours, the whole nine yards. And not just with one band. She is a member of multiple groups and also collaborates with other musicians as a performer and producer. I’ve been a fan of The Autumn Film for years, but it turns out that’s only a small piece of her musical portfolio. Other groups she’s part of include Moda Spira, Page CVXI and Sola-Mi.

Follower her on Twitter @thetifah, then listen in to learn what it’s like to be a successful professional musician.


Download mp3 or get it on iTunes or Stitcher

The show opened with “Because We Are,” one of my favorite songs from The Autumn Film:


…And it closed with a song I just discovered: “Trust Falling” by Sola-Mi. Get it on Noise Trade here.

PS: Rather than commenting here, please give Semi-Random Walks a review on iTunes.

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Semi-Random Walks # 39: Michelle Terrell, the Pistol Whip Hippie

michelle_in_officeMichelle Terrell is a force of nature. I’ve been following her on Facebook for a few years and you should too. Listen to the episode to hear how she went from being a victim to a force for good in the world.

Also make sure to check out her Integrated Man series.

Download mp3 or get it iTunes or Stitcher

PS: Rather than commenting here, please give Semi-Random Walks a review on iTunes.

You can also give me more detailed feedback by completing this short listener survey.

 

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Semi-Random Walks #38: Myles Goldin

myles-goldinMyles Goldin is a performer and teacher. Among other things, Myles teaches improve through the Boulder Improv Collaborative, which is how I met her. She also teaches public speaking and gives workshops through Presence Academy and How to Fail Brilliantly.

(Aside: I hired Myles to coach me when I first started this podcast. She was a great teacher in helping me develop a voice, both technically and in terms of character. Thanks Myles!)

The episode opened with Beck’s Cold Brains and the story of the sexiest sales call I have ever received. It closed with Steve Martin’s King Tut.

Links to some of the things we discussed:

Download mp3 or get it iTunes or Stitcher

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Semi-Random Walks #37: Scott Adams, creator of Dilbert and big time failure

Scott AdamsScott Adams, of course, is the creator of Dilbert, but that’s not all. He’s tried (and often failed) at lots and lots and lots of things in his career, ranging from video games to restaurants to frozen burritos. His 2014 book How to Fail at Almost Everything and Still Win Big documents them in detail as well as providing a realistic and often amusing approach to self-help.

Scott’s a very original thinker. His blog is full of thought experiments and contrarian thinking. Sometimes it attracts “outragists,” but luckily for us Scott soldiers on.

Follow him on Twitter @ScottAdamsSays

Download mp3 or get it iTunes or Stitcher

PS: Rather than commenting here, please give Semi-Random Walks a review on iTunes.

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Semi-Random Walks #36: Emily Best, founder of Seed & Spark

Emily BestEmily Best is founder and CEO of Seed & Spark, a kinda sorta crowdfunding platform for filmmakers, but it’s much cooler than that. Instead of just asking for money, filmmakers can ask for… stuff! Like props and makeup and locations. (Money too, of course.)

Listen to hear how Emily went from wannabe doctor to Jazz musician to filmmaker to creating an entire film platform.

Follow Emily on Twitter @EmilyBest

A lot of interesting stuff came up in the interview. Here are a few links:


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PS: Rather than commenting here, please give Semi-Random Walks a review on iTunes.

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Semi-Random Walks #35: Kristen Wheeler

Kristen WheelerKristen Wheeler is a coach and speaker. She’s also the creator of Native Genius, a strengths-based approach to career development. Learn how an improper understanding of passion can actually mislead you in trying to figure out your life’s purpose, and especially listen as Kristen demonstrates the power of vulnerability in response to something I said that could potentially have been  negative trigger.


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PS: Rather than commenting here, please give Semi-Random Walks a review on iTunes.

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Semi-Random Walks #34: Steve Swoboda

Steve SwobodaSteve Swoboda is co-founder of SpotXchange. Steve’s experience prior to founding SpotXchange includes founding Booyah Online Advertising and senior management positions at two other startup companies (Ereo, Inc. and ProSavvy, Inc.), serving as chief financial officer of iBelay LLC, a venture capital firm investing in seed stage companies, and public company experience as director of corporate development for MessageMedia (which is where we met).

Find him on LinkedIn.

The show opens with a remix of Iron Maiden’s Number of the Beast and closes with Wrathchild, also from Iron Maiden.

Download mp3 or get it on iTunes or Stitcher (Android)

PS: Rather than commenting here, please give Semi-Random Walks a review on iTunes.

You can also give me more detailed feedback by completing this short listener survey.

 

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